It Had to Be You
by JessMW
Summary: It's the Roaring 20's, and accountant Castiel Novak has moved to Boston for a change of scenery and to set up a respectable business. But when he witnesses a horrific crime one night and gets dragged before up-and-coming mob boss Dean Winchester, Castiel finds his life going through many more changes than expected-and not all of them bad. Story hopefully better than the summary:P
1. Chapter 1

_**Author's Note: **_**Hello! This is the first chapter of my first 'Supernatural' story. I know it kinda sucks and I'm sorry for that, but I'm new at this. Feedback is more than welcome. Let me know if you like it enough for me to continue, and thanks for reading!:-)**

Chapter 1

Castiel Novak gripped his briefcase tighter and muttered a curse as he maneuvered his way through the busy Boston streets. Louis Armstrong wafted through the air from a nearby diner, but Castiel barely heard. Right now, he was just trying to get to work. He didn't regret his move, but Boston was a far cry from the sleepy little Illinois town he'd come from, and this part in particular took some getting used to. People rushed passed him, bumping into Castiel and each other without a second glance. Moments like this made the accountant that much more grateful for the short walk from his apartment to the office. He ducked into an alley behind the building and went through the back door that led into his office, a medium sized square with a desk and a few file cabinets. Once there, Castiel leaned back against the door and sighed. The building itself was nothing special; just one small brick one among the thousand or so others in the smoky metropolis. But, it was what Novak had called his second home since arriving six months prior; it was his business, and he was proud of it. _Novak Accounting_. He hung up his trench coat before sticking his head into the front lobby to greet the secretary. He smiled. She was always here early. "Good morning, Sally."

"Mornin' mistah Novak. You missed a call, by the way." Castiel glanced up at the clock on the wall.

"Already?! It's five after eight; we don't even start taking calls until eight-thirty." Sally simply shrugged. "Tell it to mistah Johnson. I told him to call back in thirty minutes."

Castiel sighed. "Fine. Guess I'd better get a move on. Thanks, Sal." The secretary nodded and, with a pop of her gum, went back to whatever she'd been doing. Castiel went to his desk and organized random things in preparation for the day. It was going to be hectic, he could tell; it almost always was. He reclined in his chair and enjoyed the few minutes of silence in the morning's rush. He was a good accountant—great, in fact. Brilliant with numbers and good with people. That was one thing that he could offer customers that his larger competitors often couldn't; a personal touch. That friendly, small-business feel. But it was hard; it had been hard not only to move here, but to find this building, hire his small staff, and attract customers. Six months later, things were finally evening out; he didn't make a fortune, but he was building a respectable clientele base and was happy with the direction his life was heading. He was startled out of his thoughts by the phone ringing. He took one last long-suffering look at the clock; just past 8:30. He cleared his throat and picked up. "Novak Accounting? Yes, good morning Mr. Johnson, how are you?"

…

Castiel yawned as he turned the key in its lock. It was 10:00pm. Sally had gone home hours ago, though he'd had to stay late. He'd gotten a few calls from interested, potential clients and was thinking of them as he bundled his coat around him. It was autumn in Boston; the air was crisp and the wind was starting to get chilly. Suddenly, Castiel stopped and squinted. Way up ahead, two cars were stopped. Men in dark suits were standing around them. No, they were standing around one of the men, specifically. Castiel got a sinking feeling in his stomach. Something wasn't right. One of the men pushed the guy in the middle to his knees. Castiel could hear their voices rising. The man on the ground held up his hands in defense, and Castiel was debating what to do when the unmistakable pop of two gunshots shattered the stillness of the night. Castiel froze as he watched the man flail violently and then fall to the ground. Castiel's breath hitched, as if he'd been punched in the gut, and he shuffled backwards. One of the dark-suited men looked up and went rigged. The rational side of Castiel's brain kicked in, then, and he was able to form one coherent thought:

_Run._

And so he did. He took off in the opposite direction, heart pounding as he cut through back streets and alleys. He had no idea where he was going, but with a nauseating feeling of dread he realized that he'd just heard the screech of car wheels. He ducked into a dark passage between two buildings and waited. He waited until he heard nothing; he waited until he could no longer hear his heart beat in his ears, and then slowly, shaking, Castiel peeked out. Nothing. He took a few tentative steps out and ducked behind a dumpster. He looked around again before setting out at a brisk pace in what he guessed was the right direction, incomplete and broken thoughts racing through his head. _I need to get home. No, I should go to the police station. But I don't know where that is from here; maybe I should just wait until I get home and then call-_

He didn't get to complete his thought; because out of nowhere, two huge, bright headlights shone in front of him. He could see two figures inside the vehicle. Castiel turned, ready to run again, only to be met with the second car just pulling out of a vacant lot behind him. It had been sitting quiet and hidden in the shadows; he hadn't even seen it. Fear and helplessness like Castiel had never know before washed over him as they all turned off the cars—save for the headlights—and got out. The driver of the car in front of him stood in front of it. Castiel squinted into the bright headlights and held up a hand to block the light. He could only partially see the man before him; he was of slight build and height, and that was all he could tell at the moment.

"Pl…Please. Don't. I didn't-

"Shut up. You're in deep shit trouble, pal."

"Please, Mister. I didn't see anything. I'm was just trying to get home…"

"You realize lyin' ain't gonna help you, right?" This came from someone behind him. Castiel's throat felt like sandpaper. "I won't say a word—honest, I won't!" The man stepped forward, and Castiel could see now that he was a blonde man of slight build.

"But we have a little problem. I believe you saw our faces. And our cars. You see where I'm going with this?" Here the man pulled out something metal and shiny, and Castiel's heart stopped. Suddenly, one of the men behind him spoke up.

"Milligan?" And the man with the gun glanced over at the speaker angrily. "Not my real name, you stupid fucker! Goddamn, you're lucky we're about to kill this bastard anyway, you _moron_!" Castiel almost let out a whimper, but the man behind him continued anyway. "Ya heard what he said, though? Make it clean; just one body. Do it and get out." The one Castiel now knew to be Milligan responded through gritted teeth. "But something has clearly come up. What, you wanna go back to the Boss and say—

"I'LL SCREAM!"

Castiel's outburst surprised even himself as his survival instincts kicked in. He had to try; he had to give it a shot, do _something_, or he was definitely not going to make it out of this.

The men jumped, and Milligan raised the gun and cocked it in one quick movement. "I fucking dare you. You shut your damn mouth right now or-"

"Hello? Hey, who's out there?" A light came on in an apartment far above them. Milligan cursed under his breath and gave Castiel a death look. He motioned with the gun. "I swear to God…"

But just as the accountant opened his mouth and barely got one syllable out, a swift punch to the ribs silenced him. He doubled over and groaned in agony. A hand clamped down over his mouth and he was dragged over into the shadows. He fought and made as much noise as possible, praying that the woman above them could hear. Another blow to his head ended his attempts. After a few minutes of breathless silence, the light in the window went out, and Castiel could have cried. Through a dizzy haze, he heard hushed arguing.

"We gotta go. We can't stay here, and we're already out way past the time the Boss expected us back. We screw this up and we're dead, Milligan."

"Christ, you don't think I know that?! Crap. Alright; put him in the car. We're taking him back with us. We'll let Winchester decide what to do with him." The enormous relief Castiel felt was short-lived when he realized that he was not going to get to go home. Two of the men roughly hauled him to his feet and dragged him to their car. The clicking of the doors closing deepened his despair, and all he could do now was wait. Ride and wait. He leaned his throbbing head back against the seat and squeezed his eyes shut.

…

They were stopped; Castiel's eyes popped open. The headache was still there, but he felt much more clear and alert—alert enough that his heart sank when he saw that he had not, in fact, been simply dreaming this nightmare. The driver of the car his was in came around and yanked him out.

"Let's go. Quick."

Castiel looked around; he didn't even recognize which part of the city they were in now. They were parked in front of an old, greyish-looking building; it was hard to tell in the dark. He froze when they got to the doorway but was rudely pushed forward. Upon entering, he noticed a pool table; a refrigerator; and a small card table off to one side. His escort put an impatient hand on his shoulder.

"I said _move_, dammit!"

Castiel quickened his steps as he was guided to a large back room. Several men were there; some of them he recognized as his kidnappers, a few he didn't. Milligan stood in front of a stranger sitting at a desk, blocking Castiel's view of him. He could hear a voice; a deep voice, low and gravely. Castiel was forced down into a chair. His heart nearly pounded out of his chest, and he could feel himself sweating through the clothes that just a little while ago felt so comfortable in the cool November air. Milligan turned at the noise and then moved out of the way, revealing the other man. He stood. This man was tall, with broad shoulders and muscular build. He wore a fitted charcoal gray suite with a matching fedora. But the thing that jumped out at Castiel was his eyes. They were slate-green and neutral, but their undertones gave away all kinds of unspoken threats. Castiel met them for an electrifying, terrifying moment and then looked away.

"Who are you? Where am I?" Mumbles of amusement circled around the room.

"Hey, has anyone told you to talk yet?!" One voice boomed. Castiel heard movement and flinched, fearful of another blow. But the mystery man in front of him raised a hand and the room was silent once more. He leaned backwards against the front of the desk, hands supporting him on either side. He never broke eye contact. Every time Castiel glanced up, he was met with that steady gaze. The man smirked slightly.

"Me? I'm Dean Winchester. I run this whole shebang, and right now that's all you need to know about me. That, and, since my associates here apparently can't do jack-shit right, I've been put in the awkward position of deciding whether or not you get to walk out of here."

At that exact moment, in that dimly lit room, Castiel regretted leaving Illinois with every fiber of his being.


	2. Chapter 2

**A/N: Oh my gosh, followers?! And people are favoriting my story? Wow, guys, really wasn't expecting that:-') Thank you so much! Keep 'em coming! Follow if you like it, and don't forget to review! Again, any review, including criticism, is encouraged! **

Chapter 2

"What's your name?"

Castiel swallowed hard. "Novak; Castiel Novak."

"Well, Cas, seems you're in quite the bind." Dean lamented, lighting up a cigar. He held one out to Cas and raised his eyebrows, but the terrified man shook his head. Dean shrugged and took another puff before continuing.

"Here's the thing. This whole operation tonight was supposed to be short, sweet, and simple. But as I've said, nothing can go smoothly with my crew, and unfortunately you've become collateral damage. I don't want another body on my hands. So…give me a reason why this shouldn't end badly for you." Cas heard a click beside him, and he didn't have to turn to know he'd be looking down the barrel of a revolver if he did so.

"I won't tell a soul. I _swear_!" His voice broke as he begged.

Dean shook his head with an exaggerated expression of sympathy on his face. "Aw, listen to that, fellas; he _swore_. Make that a pinky-swear and you might have a deal." Castiel pursed his lips.

Before he even knew what he was saying, the words were out of his mouth.

"I can help you! I can be an asset! I believe I can be of great benefit to your…organization."

"Oh?" Dean responded flatly.

"I'm an accountant. I own Novak Accounting over on 5th. I can help you; I can manage your money, your accounts, no questions asked by anyone. I can keep the government out of your business. Your money business, anyway."

"You any good?"

"I'm brilliant." Castiel rasped. Dean ran his thumb down the side of his mouth thoughtfully, and then turned to a man whom Cas hadn't noticed before, in a darker corner behind the desk. He was taller than Dean, and more muscular, but he didn't quite have the commanding presence Dean did. His posture was more relaxed, and when he stepped out of the corner his hands were tucked leisurely in his pockets. He went to Dean's side and whispered in his ear, letting a hand rest on the shorter man's shoulder. Dean listened for a few minutes, nodded, and then whispered something back. They broke, and the stranger's brown eyes flickered over to Cas. The prisoner thought he saw a glimmer of sympathy.

Dean turned back to him, and for the first time that night, Cas met his eyes and held his gaze. He seemed to be boring into the accountant's soul, searching. Cas did the best he could to appear confident and sure, but he struggled to keep from trembling. After what seemed like an eternity, Dean motioned to the gun-wielder, who then dropped his arm, and Cas let out a breath he didn't realize he'd been holding.

"Ok. Alright, Mr. Cas. You've piqued my interest and talked your way out of trouble-for now. But you'll be hearing from us." There was movement, and Cas was being guided upwards again to stand on numb, shaky legs. Dean walked over to him, smiling broadly, and clasped him on the shoulder. Cas resisted the urge to jerk away. "Tonight's your lucky night, my man." He then addressed a burly, dark haired man in the room. "Logan. Take him home." Cas shot Dean a panicked look when one of the driver's from earlier came forward. Dean rolled his eyes.

"He ain't gonna hurt you, ya pansy. Now go on before I change my mind."

He then went back to his spot behind his desk and scooted his chair back so that he could put his feet up. As Castiel was being escorted out, he suddenly remembered something Dean has said.

_Cas? _

Did he just get a new nickname?

He glanced behind him once more. Winchester was absently playing with a pen, seemingly lost in thought. When he noticed Cas staring, though, a slow, wicked grin spread across his face, and he winked. It was quick and discreet, but the newly freed man was suddenly glad for the shoddy lighting. It hid the blush creeping up the back of his neck.

…

The car pulled up in front of Castiel's apartment building. He sat there for a moment, until his driver, Logan, spoke up irritably. "You gettin' out or what?" Castiel snapped to attention.

"Oh. Yes. Um. Is…is that it? You're letting me go?" The man turned to him.

"Why? You wanna go back just to be sure?"

"No!"

"Then yeah, get outta here.

"You know, you're one lucky son of a bitch," he added as Cas slammed the car door shut.

"I guess."

Logan grunted. "You guess? You could be wearing concrete shoes right now, sunk to the bottom of a river with half your face blown off and you _guess_?"

"Fine, yeah, I'm lucky."

"Just don't try any funny business. Winchester's not a guy you want on your trail." And with that, he sped off, leaving Castiel to stare after him until his tail lights disappeared over a hill. He made his way up to his apartment; when he made it in, he collapsed on the couch and buried his face in his hands. He pulled them away after a while, wiping away moisture from under his eyes. He looked around his home in disbelief, a surreal feeling fogging his brain. He squinted up at the clock. 1:00am. Sighing deeply, he stretched back out on the couch as the adrenaline wore off and left him with unforgiving exhaustion. Cas closed his eyes, but for a long time was unable to see anything but two hard green orbs staring back at him, and the gleaming metal of a revolver.

…

When Castiel awoke the next morning, it took a moment for him to fully wake up, to remember where he was. Only the deep ache that had settled into his bones reminded him of the previous night's events, and it all came rushing back. Cas sat up and rubbed the back of his neck. He stood and stretched, catching a glance at the time; he froze, eyes widening in alarm. It was 8:00am.

"Holy hell!" Castiel dashed about the apartment, gathering up fresh clothes and wrestling into them as quickly as possible. He straightened up his hair as best he could; he had a slight shadow along his jawline that needed shaving, but that would have to wait. Briefcase. Where had he put…? And then it dawned on him. Castiel let out a breath in frustration. He must've dropped it during last night's surprise sprint. Great. He pulled on his coat and nearly stumbled getting down the stairs. Once out onto the street, he realized he'd become one of the people he'd hated, pushing and bumping others with equal vigor. On the way to his office, Castiel's mind worked over different solutions; maybe he could go to the police. If he went quickly, right after work and explained the mess he was in, they could—

Castiel stopped dead in his tracks. He was staring at the back door of his office, seeing but not believing. There, on the stoop, waiting for him, was his briefcase. Castiel felt the blood rush from his face. Slowly, he reached out and picked it up; it looked fine. In fact, it looked like it may have even been dusted off for him. He got it inside and sat down at his desk. He was about to open it when Sally lightly knocked. He jumped.

"Sir? Everything alright? You're never late." She asked, brow wrinkled in concern. Castiel managed a small smile.

"Oh, yes. Everything's just fine, Sally. I, ah—woke up feeling a bit ill; nothing to worry about, I assure you. But could you bring me a cup of coffee, please? It would really do the trick." She left to get the coffee and Castiel turned his attention back to his briefcase. He opened it and was surprised to find everything in order. That's when he noticed the note.

_Mr. Novak,_

_Thought you might be looking for this at some point._

_ -D.W._

The note was simple and short, but Castiel got the intended message loud and clear.

_Just keeping you on your toes. _

He snapped the top shut and then laid his head down on the briefcase. He didn't even notice when Sally slipped in, set a mug on his desk, and then quietly slipped back out.

…

The next few days passed without incident, and Castiel was starting to relax just a little. Perhaps they'd leave him alone, or forgotten about him. But a knot in his stomach told him that that just wasn't true. That fear was confirmed, when, one Friday afternoon, almost a week after the incident, a familiar car pulled up alongside Castiel as he was walking home. The driver leaned over to roll down the window, and Cas could see that it was Logan.

"Get in." The command was easy enough, but Castiel didn't move.

"What are you, deaf? Get in. He wants to see you." Castiel suddenly got a quick mental image of Dean Winchester tilting his head in detached amusement at his desperate pleas, and he shuddered as he climbed into the passenger seat. They were quiet for a while before Castiel spoke.

"Can I ask where we're going?" Logan glanced at him.

"Boss Winchester asked for ya back at the hideout."

Cas's heart began to pound at the thought of returning to that place. He gripped his leg tightly, nails digging into the fabric of his pants, and tried to reason with himself. _He said he'd contact you. If he had changed his mind and wanted something different, he would've done something about it much sooner._

When they pulled up, Cas waited on Logan to lead the way. When he hesitated again once they'd gone inside, Logan looked at him blankly.

"What? I'm not your goddamn butler. I think he's in the back, go find him yourself."

Cas bit his lip but did as he was told. It wasn't a big building, and he was surprised to find that it wasn't nearly as intimidating when fully lit. Even Dean's office, where he'd begged for his life, didn't quite have the same effect. Still, he wasn't eager to step back inside it any time soon. He turned down a short hallway, towards the sound of voices. He stood in the doorway, nervously shifting his weight from one foot to the other until Winchester noticed him.

"Cas Novak! There ya are, come on in."

Cas went in and sat across from Dean and a man with a short, scruffy beard who gave Cas a friendly smile. The accountant waved back awkwardly.

"Cas, this is Chuck. I've told him about your…situation. Chuck here handles most of our legal problems pretty damn well, but I gotta admit our finances are crap. That's where you come in," he explained. Cas looked over at Chuck, who was fishing something out of his bag. He came back up holding an accordion binder filled with papers and files. He plopped it down in front of Cas. He proceeded to look through one of the folders, then raised his eyebrows and looked back up at Dean.

"Well. They are a mess; but not unsalvageable. Let me come up with a base plan for you." He shrugged. "I'm pretty sure I can help."

Dean nodded. "Alright. You and Chuck are gonna-

At that moment, another man poked his head in the door and Cas did a double take when he saw that it was the same guy Dean had consulted about his fate several nights ago.

"Dean? You got a minute?" Dean turned to the stranger.

"Sure, Sammy. You guys get started, I'll be back in a little while." He left, following Sam down the hall. Cas looked at Chuck quizzically.

"Sam. Dean's younger brother," Chuck supplied helpfully.

"Oh," Cas replied in a curious tone. "Do they…are they both in charge, here?"

The other man chuckled. "Nah, man. Dean's the Boss; or he is, now that Singer's goin' downhill fast. Dean tries to keep Sam outta most of the really dirty, brutal stuff. You won't see him around here too often. He was here the night you were on an unrelated matter. Lucky for you, huh? I think he's at least partly responsible for you being here."

Cas's face became somber at the memory, and Chuck debated before continuing.

"Cas? I'm gonna let you in on a few things, because I think it's necessary to your continued survival that you know a little more than you've probably been told. We're all fairly new here; Dean came into his position a little quicker than we were expecting-we all did." He patted the files. "Hence this headache. I can't go into it much deeper than that, but let's just say you came along at a really convenient time."

Castiel nodded. "I understand. I'm only alive because…

"We really needed a money guy. To be honest, any other Boss probably would've put a bullet in your head without a second thought, but like I said, Dean was in a tight spot."

Castiel wrinkled his forehead. "Why are you telling me this?"

Chuck leaned forward. "So that you better understand the position Dean, and in turn you, are in. Dean may not be extremely experienced at this yet, but he's getting there. I just want to warn you that trust, loyalty, and respect are big around here, Cas, real important to Dean. Once you're in, you're like family, but he won't hesitate to put someone in their place. I just want to know what you're dealing with."

Castiel digested all this new information. "Thank you, Chuck; that…actually does help."

Chuck nodded sympathetically. "Sure, man. Thought you deserved not to be left _completely_ in the dark." He glanced back down at the binder and crinkled his nose. "Guess we'd better dive in here."

Cas opened a file, newly resolved.

_You're in this now. Survival._

…

An hour and a half later, Chuck was yawning and Cas was bent intently over some papers, the sleeves of his dress shirt rolled up to his elbows. He'd shed his trench-coat and hung it on the back of the chair. Dean strode back in.

"Sorry 'bout that, fellas. So, where we at? How we doin'?"

Chuck arched his back to pop his spine and looked up at Dean.

"I like the way this guy thinks, Boss, I gotta say. Show 'em, Cas."

Cas shrugged humbly. "It wasn't easy, but we were able to work out a large portion of it. If you'll allow me to take the rest of it home and to my office, I can keep going." He handed Dean a newly put together file. "That's the plan right now in a nutshell. It's not quite finished, but it's a start." Dean took the file and opened it.

"You know that car wash for sale a few streets over?"

Dean nodded as he skimmed over a piece of paper.

"Buy it. Buy it and find find someone you trust to run it for you."

Dean looked at Cas like he was crazy.

"Boss, the IRS gets suspicious when there's unexplained money involved, and then even I may not be able to get you out of a scrape. I'd take his advice; we need a cover and we need it bad, at least until we become more established," Chuck interjected.

Dean bent slightly and drummed his fingers on the table. After a few minutes, he spoke again.

"I'm not a numbers guy, but if you and the accountant say this is a good idea, well, who am I to argue? Alright, fellas; I'll make it happen." His eyes fixed on Cas.

"Nice job, new guy."

Cas smiled slightly and nodded once. Chuck stood.

"Am I done, Boss?"

"Yeah, Chuck. See you tomorrow, have a good one." He bade Cas good-night before leaving, and then it was just Cas and Dean in the room.

"You're really happy with what I've done so far?" Cas asked hopefully. Dean walked over to him and crossed his arms over his chest.

"Cas, if I wasn't, you'd be the first to know. And I trust Chuck."

Cas felt an enormous weight lift off his shoulders. He also felt like he actually could've cried, but instead just breathed a sigh of relief and began gathering up his things. Dean watched him with interest.

"What brings you to Boston, Cas? You said you haven't been here long."

Cas blinked. "Oh. Yes, I've only been here about six months."

"Where you from?"

"Illinois."

Dean whistled. "Big move. Why Boston?"

Cas smiled faintly and looked down at the table. "I'd heard about everyone going to the big cities; all the poets, the musicians. I wanted to be a part of it. I think mostly I just wanted to get out of Illinois," he laughed. "I knew a lot of folks who went to New York, but I'd always heard Massachusetts was prettier, and a little cheaper. So I upped and moved to go on my own sort of adventure," he shrugged. Cas had forgotten that Dean was there, listening quietly; he'd lost himself in his own story, perhaps remembering his original hopes for moving here, or maybe thinking of his home state and family. When he looked back up he was startled by the intensity of Dean's gaze, and his own blue eyes still had a dreamy shine to them. It must have caught Dean off-guard, too, for something changed in his expression. His features softened, and his lips parted slightly. Suddenly Cas was aware of how close Dean was; he was now standing almost over him, leaning against the table. Cas found that he was too intrigued by the change in Dean's solid green eyes to break contact. Dean's gaze eventually traveled lower, seemingly to settle on the other man's mouth, and Cas felt a familiar heat in his face.

The corners of Dean's mouth twitched in amusement, and he opened his mouth to speak when a voice startled them both.

"Hey, Boss, I-

Milligan stopped short in the doorway, surprised when Cas quickly jumped up from the chair he'd been sitting in.

"What's he doing here?" Milligan asked, cutting his eyes at Cas.

"Cas is on probation, but he's proving himself pretty quickly, aren't ya Cas?" With a grin, he looked back at Cas and winked slyly, yet much more playfully than the first time. The brown headed man swallowed; his throat felt very dry.

Milligan still looked unhappy, but he let it go. "I talked to that go-between. When you're ready."

Dean nodded. "Be there in a minute." When Milligan was gone, Dean turned back to Cas, who was hastily putting on his trench coat and refusing to meet Dean's eye again. Dean raised his eyebrows.

"I should get home—if we're done here," Cas said.

"Are we?" Dean asked teasingly, smugly relishing the pink that stained the other man's face at his words. When Cas couldn't seem to figure out how to respond and looked genuinely flabbergasted, Dean couldn't hold back a long, hearty laugh.

"I'll have Logan drive you, man," he said, a grin still splitting his face.

"Oh, no-he doesn't have to. I'll take the bus."

"You sure?" Dean asked.

"I am sure. I'll see you…?

"Soon," Dean said. Cas nodded quickly and eased past Dean.

"Night, Cas," Dean called after him.

"Good night…um, sir," Cas said meekly, ignoring the odd looks from Logan and Milligan on his way out.

…

When Cas got home, it wasn't that late—only 9:00pm—but he was beat. His reeling mind settled down as soon as he hit the sheets, and he was out in a matter of minutes.

Cas's subconscious produced no images that night as he slept; only a single sound rose to the surface of his sleepy brain. A gravely, rolling laughter that stretched softly over every corner of his dreams.


	3. Chapter 3

Chapter 3

**A/N: Not much to say except thanks for the follows! They make me very happy:-) Here's chapter 3! Hope it's to your liking, and don't forget to review! I'm going out of town and won't see them for a few days, but they're still appreciated!:-)**

After a few months, Cas managed to settle into a fairly predictable routine. He'd go to work and resume his life as usual, and every couple of weeks he'd get a note from Dean or Logan would randomly pull up and take him to a meeting place. He couldn't exactly call it comfortable, but at least he knew what to expect now. Dean's underlings gradually become more lax around him, and Cas in turn became less guarded and tense in their presence. He had become friends with Chuck, was on good terms with Logan, and was fine with Sam, though Cas rarely saw the younger Winchester. Milligan was the only one who still genuinely gave him the creeps, but most of the time they simply avoided each other.

And then there was the Man himself; Dean continued to remain somewhat of an enigma. He was all at once the protective big brother, the street-savvy mobster, the poker-faced negotiator, the charismatic but guiding leader, and the tough, at-times-harsh boss.

Cas found that he couldn't help himself; he was captivated by Dean's very persona when he was near, to the point of not being able to get anything done. The accountant was used to math and numbers, and straightforward problems with clear answers. Dean's mysteriousness was far and above out of his comfort zone. The confusing flirting didn't help either. Cas couldn't tell if Winchester was serious or not; sometimes he was playful and teasing, and other times Cas would catch Dean staring at him in a way that made the accountant noticeably squirm. The strange thing was, Cas wasn't sure what he wanted it all to mean; he could reluctantly admit that he was a little enamored with the man, but there was still the ever present reminder in the back of his mind that these people were criminals—_dangerous_ criminals. Had he not watched Milligan shoot a man in cold blood? And Cas was technically among them now. He tried not to dwell on it, however, as the thought often kept him up at night.

Cas was surprised and worried one Friday evening when, just a week after their last meeting, he exited his office to find Logan already waiting for him, reading the paper in his parked car. Cas jogged over. He tapped on the window to get the driver's attention, and Logan reached over to unlock the door. Without having to be told, Cas climbed in.

"What's wrong?" He asked anxiously. Logan shrugged.

"Got me. Winchester just called a big meeting, then asked me to get you and make it snappy." He glanced over at Cas's expression and added:

"He didn't seem mad, kid. I don't know what's up, but he looked ok when I left, so…

He trailed off and Cas slowly nodded. Dean had been acting more secretive than normal their last few meetings, and was in and out of the room or completely absent from Cas and Chuck's work. Several times Cas heard him speaking in hushed tones to someone on the phone. When he _was_ there, he asked a ton of questions and wanted copies of notes. Cas was curious, but he relaxed as long as Dean wasn't angry or upset with him. When they got to the hideout, Cas hastily made his way in, Logan in tow. Dean, Chuck, Milligan and Sam were in Dean's office. Dean was seated but rose when Cas and Logan entered. Cas quickly searched the faces of everyone in the room, but they also seemed to be in the dark. Chuck shrugged helplessly when he saw Cas's questioning look. Cas's gaze found Dean; his expression gave nothing away, but the corners of his eyes crinkled as if he were suppressing a smile. The room was deathly quiet, and all of them being in the same room, in front of Dean, reminded Cas of that night months ago. He'd more or less gotten over the trauma, but Dean's office was giving him a prickling sense of déjà vu.

"Now," Dean began, clasping his hands behind his back and slowly pacing the room. "As you all know, I've been in the process of working out a business deal that would bring us a significant amount of cash."

Everyone else nodded but Cas continued to stare. He'd heard snippets here and there, but knew no details.

"And it's no secret that our finances took a huge hit last year. It's hard to get people to go in with you when it looks like you can't manage your money, and I didn't think we'd ever get our heads above water." He stopped in front of Cas.

"Until Cas here came into the picture. Because of the way he and Chuck whipped our books into shape, I am more than happy to announce that as of 3:00pm today…a nice deal was struck up involving some other high-ranking gangs. We'll be getting nice chunk of change to work with them on some things coming up."

Whoops and hollers filled the room; Sam embraced his brother and patted him on the shoulder when he pulled away, grinning. He even shot Cas a kind, approving look. Logan and Milligan clasped Dean's hand and exchanged congratulations. Milligan still wouldn't smile at him, but he did give Cas a slight nod. Cas frantically looked around, confused. He jumped when Chuck slapped him on the back, a huge smile on his face.

"How 'bout that, man?" He asked.

Cas shook his head. "So…we did good? This is all good news?"

Chuck chuckled. "Good? Cas, this is _great_! This is huge for us. All thanks in no small part to you, bud." Cas looked down sheepishly.

"Oh, well, I'm just glad I was able to-

"Cas." Dean's voice made Cas's head snap back up. Dean held out his hand. Cas took it, and Dean enclosed Cas's hand within both of his, shaking it vigorously.

"Great job, Cas. I mean it, thanks. You're freakin'amazing, man." Cas blushed, palms becoming clammy in Dean's firm grasp.

"Thank you, Sir. I'm…happy for you." Cas wasn't exactly sure how to respond to the situation. The vain part of him was proud to have done a job well; the upstanding citizen in him was all too aware of the fact that he'd just aided highly illegal activities. Dean either ignored it or didn't notice, though, and gave Cas's hand one last squeeze before addressing the rest of the group.

"Boys, we can't get too cocky, but I do believe this calls for some celebration." Dean waited for the jovial sounds of agreement to die down.

"Everyone take the night off and don't worry about checking in 'til noon tomorrow. Be ready to hit this hard afterwards; this is our chance to prove ourselves. This is what we've worked our asses off for. But…enjoy yourselves for now—oh and remember, if you get in trouble and get yourself thrown in the drunk tank or something, I don't know you. Don't call me." He smiled slightly at the excited rustling and scuttering from the room and turned to Sam to speak to him for a few more minutes. Once everyone was gone and Chuck had shaken Cas's hand one last time, Dean strolled up to Cas.

"What'cha got planned for tonight, Cas?"

Cas blinked.

"Oh, I thought I'd just go home and-

"No, no, no. Man, we gotta celebrate and get you outta work and home for a little while. You ever been partying in Boston?"

The other man shook his head.

"Well, we're gonna change that. There's a whole side to Boston you ain't seen yet, Cas. A whole different world out there, and I'm going to show it to you." He looked Cas up and down, noticing his stiff work clothes and trench coat.

"You may wanna change first. How 'bout you go home and get ready and I'll swing by and pick you up in an hour."

It was more of a statement than asking Cas's permission, and the accountant could do nothing but nod dumbly.

"Great! See you then." He lightly slapped Cas's arm on his way out and Cas left in a haze. He wasn't sure how all this had happened so quickly, but apparently he now had plans for the evening. With Dean Winchester. He groaned and again wondered how he gets himself into these situations.

…

Cas looked down at himself one last time as he stepped out onto his building's front stoop to wait for Dean. He had changed into what he hoped was a little less stuffy, but at the same time nice, having no idea what one wears for a night on the town with the local mob boss. He fiddled with the buttons on his shirt and contemplated changing again when he heard a sound coming down the street and froze. His eyes widened and his jaw dropped slightly. There was the most beautiful car Cas had ever seen pulling up to the curb. He recognized it as a Duesenberg—jet black and sleek, the kind of thing he had only _dreamed_ of, and God was it a beauty. He stared in slack-jawed amazement until another sight took his breath away and stole his attention more than a car ever could.

Dean stepped out of the driver's side and came around to the front of the automobile. He was wearing a navy blue suit with shiny black shoes, a black tie, and a navy blue fedora with a black band around it. Cas took him in; he looked damn sharp in the tailored suit, seemingly made especially to fit Dean's broad shoulders and hug the slight curve of his waist perfectly. And the color made his green eyes absolutely _pop_. Cas felt something in his stomach flutter and tried to force his brain to come up with something to say. Dean quirked an eyebrow.

"Cas?"

_Too late. _

"Um, your car," he floundered. "It's…simply stunning."

Dean grinned proudly and patted the hood.

"Yeah, this baby was a gift to my uncle Bobby. Me and Sam have it now. Mostly me," Dean was quick to add.

"Well. It's amazing," Cas said, jerking his attention back to the car.

"Thanks. You should try riding in it."

"Oh! Yes, I suppose we should go."

Dean got back behind the wheel and Cas carefully scooted in beside him. He felt out of place, like he had no business being in such a machine. But Dean just revved the engine back up and pulled away from the curb.

"Is it just us?" Cas inquired when he realized that Sam at least hadn't come with Dean.

"Yep. You give these guys free time and they all scatter to the four winds. I think the first thing Sam did was set up a date with some broad he's been talking to."

Cas nodded. So it would be just he and Dean. And that was…fine. Cas cleared his throat.

"So where are we going?"

Dean grinned mischievously at him.

"You'll see."

Cas leaned back against the plush seat and stared out the window, trying to track where they were. Dean was taking him to inner Boston, and then further still. They pulled onto a street and Cas's brain was suddenly overloaded with lights and music. People flooded the streets; men who were dressed similar Dean with women in sparkling jewelry and short dresses on their arm. Cas had never seen anything like it, and he was instantly fascinated at the night and day difference from what he was used to in Boston.

"Welcome to my side of town, Novak," Dean commented when he noticed Cas's face.

They parked on one side of the street and walked across to a large, lit-up, but rather average looking building that had a simple sign out front that said "Hell's Tavern."

Cas stopped abruptly.

"Um, Sir?"

"Dean, Cas. You can call me Dean. What is it?"

"It's just…well, this place serves alcohol, doesn't it?"

"And?" Dean gestured impatiently. "C'mon. Show's gonna start in a little while."

Cas looked around nervously; what if someone he knew saw him here? Or even worse, a client, and reported it to the authorities? Of course, Cas reasoned, to mention it to anyone would also be telling on themselves, so…

"Cas? Dude, let's go. Ain't nobody going to bother us; the cops don't give a damn about this place; hell, some of them come here."

Cas pursed his lips but hesitantly followed Dean. He couldn't very well tell the guy to take him home, so why not?

They walked into a front room that looked like a typical bar, but Dean led Cas down some stairs and into the building's basement. If Cas was skeptical at first of the place's "party potential", he was in for a shock. The outside of the tavern totally betrayed the inside. The bottom room he and Dean stepped into was a hub of activity. Upbeat, fast paced music filled the room, and Cas spotted several couples dancing. There were tables with chars and booths, a large bar, ornate light fixtures on the ceiling and a dark red carpet on the floor; large red curtains hid a stage. People laughed, drank, and danced, and Cas wasn't sure where to look first. Dean gently took his elbow and led him to a back booth that still gave them a clear view of the stage. Once they were seated, Cas looked at Dean.

"I've heard of bars like this, but I never imagined…

"Pretty swanky place, huh?" Dean asked.

"But these places get raided fairly often. Aren't you afraid of getting caught?"

Dean shrugged. "Not if you do it right. Don't come every night and pick a discreet place like this. We'll be fine—you'll be fine with me."

Cas nodded but still sat stiffly. He couldn't help but take note of how relaxed Dean looked; like he was in his element here. Cas watched him lean back and rest his arms up on the top of the booth. A blonde waitress in a black cocktail dress came up to them.

"What can I get you and your friend tonight, Dean?" The woman asked, tilting her head and smiling at him.

"Two cocktails, darlin'," he answered, flashing her his own award-winning smile. Cas wondered if that grin carried as much power as his intimidation techniques; Cas guessed it probably did. In fact, he personally _knew_ it did. She batted her eyes and bounced off with a little giggle.

Dean watched her for moment and then turned back to Cas.

"What do you think?"

Cas looked around. "It's a busy place. A lot more people than I would've expected.

Dean shrugged. "People need to have their fun every once in a while. Let all the 'badness' out."

Cas considered this.

"And you? How about you, Cas? This really the first time you've ever done anything like this?"

Cas nodded shyly. "Yes. But I am having fun," he amended, not wanting Dean to think he was miserable. Dean turned his attention to the dance floor, where people where swinging and tossing partners up in the air. The mob boss watched with sparkling eyes, and at one point he threw his head back and laughed at one couple's funny dance move. His nose crinkled and the laugh came up easy, rumbling through his chest. Cas couldn't help the feeling that he was seeing the real Dean Winchester, and he smiled softly. The waitress brought their drinks then, and when she handed Dean his she let her hand graze over his. He looked up at her and winked.

"Thanks, doll," he said smoothly. She blushed and scurried off to another table. Dean chuckled lightly to himself and took a sip. Cas continued to study him and licked his lips.

"Boss-er, Dean. Why do you do this?"

Dean paused and eyed Cas, then set his drink down.

"Why am I in the business?" He shrugged again. "It's a family thing. And it's something to do; plus, when the money's good, it's really freaking great."

"But it's illegal; it's…you do things that could get you into trouble, things that are wrong."

He was worried he'd stepped over the line, but Dean simply snorted.

"Says the guy laundering money for the mob."

"I had no choice!" Cas protested defensively.

Dean leaned forward and balled his hands together on the table. "Oh? What about us? You ever stop to think that maybe we-Adam, Chuck, Logan, me and Sammy to some extent-don't exactly have a choice? That we're all just trying to play the hand dealt to us and make the best of our situations, whatever it was that brought us to this line of work?"

Cas looked down at the table. "I'm sorry. I didn't mean to offend. It wasn't a judgment, I was just curious." He took a small sip of his drink just to be doing something with his hands, but wrinkled his nose and put it back down. Dean breathed a chuckle through his nose.

"My father was involved in this our whole life." Cas's eyes flickered back up at Dean and he continued.

"We watched him wheel and deal with the best of them. He was pretty amazing," Dean lamented fondly.

"He, ah, was killed when I was a teenager. Sam was pretty young. Mom died when Sam was just a baby, so we had nowhere to go. An old partner of my dad's, my uncle Bobby, took us in. He picked up where Dad left off and I shadowed him for years. I wasn't supposed to take his place for a while, but…he got real sick last year and we had to scramble. A lot of Bobby's higher up associates bailed; Milligan and Chuck were at the bottom but suddenly had to move up. Logan was the only one of Bobby's original underlings to stick with me. Maybe he just feels loyal to the old guy, I don't know. But we're coming along. Still got some kinks to work out," he chuckled. He raised his drink again and Cas just stared. Dean's eyes had looked so far away then, so sad, and Cas felt a tug at his heart. But he wanted to go on.

"That night I was brought to you…

Dean fixed his eyes on him.

"That's an example of some of the kinks we gotta work out. No witnesses and pick the places better. Milligan will learn. He's a good kid; and determined."

"A good kid that tried to kill me," Cas muttered. '

"Yeah, about that whole thing. Water under the bridge; sure, it could've turned out bad for you, but it didn't, so move on." Cas blinked at him.

"It kind of turned out badly."

"I didn't kill you, did I? I took a chance and it worked out. You were a good save, Cas."

This touched Cas a bit, but he didn't respond, choosing to take a few more swigs of his cocktail. It went down much smoother this time. The lights suddenly dimmed, and clapping erupted from the room. Dean gave Cas a look.

"Watch this, man. You're in for a treat." Cas was about to ask what he meant when the heavy curtains hiding the stage slowly separated, revealing a young woman under a circle of light. She had dark hair, blood red lipstick and nails, and a long, clingy red dress slit up to the hip on one side. Her body swayed as she stepped up to a microphone. Dean put two fingers in his mouth and whistled. "Her name is Meg. She's something, I'll tell you."

"Hello, all. Thanks for comin' out tonight. Look at you ladies and gents, not worried one bit about those old cops." Boos and hisses went up.

"Well, let me officially welcome you to Hell's Tavern. Fellas?" She signaled to a small band to the side of the stage. The silky smooth sounds that came out of the woman's mouth silenced the room. No one spoke a word, and Dean looked captivated. Even Cas shivered when a particularly smoky note hit his ears. She owned the room for the better part of an hour. When she wrapped up her finale and blew a kiss to the audience, the lights came back on brighter. Cas squinted and shook himself clear of the trance.

"I told ya. Something, huh?" He smiled wistfully at Cas.

"She's amazing…that voice," he managed.

"Tell me about it," Dean grunted. The dance floor opened back up and was full again soon; Cas was content to people watch, but at one point Dean looked over at him. "Hey, Cas? Wanna dance?" Cas was taken off guard. Dance in public? He looked at everyone else glammed up and was reminded of how inadequately he was dressed.

"I don't know. I don't think so."

"Aw, come on. Loosen up. I'll help you."

It could've been the drink influencing him, but Cas reluctantly allowed Dean to grab his arm and lead him onto the dance floor.

"Alright, this is an easy one. More of a free-style dance; just follow me."

Cas frantically tried to keep up with Dean and the other dancers. He finally started to get the hang of it.

"That's it! You got it!" Dean encouraged from a few feet away. For the end of the song, a step with a partner was required. Dean moved to match Cas's moves and copied the other dancers' by grabbing Cas's wrist and spinning him once. They both laughed as the final notes faded out. When their laughter died down as well, Dean still had a hold of Cas's hand. Both their faces were flushed form the exertion; Cas's chest was heaving slightly, and his eyes shone from the adrenaline rush. Dean swallowed and trailed his thumb down Cas's wrist, meeting his eyes. Cas's heart rate sped up and the feeling of Dean stroking his hand made him want to sigh.

"Alright, folks, grab your partner and get ready for a slow number!"

The band leader's voice made Cas jerk his arm away. Dean seemed to also snap out of it and looked around. Everyone was too busy to have noticed anything, and Dean motioned with his head to go back to the table. Cas quickly followed and they sat down. Thirsty, they finished off their drinks and Cas didn't want to look Dean in the eye for fear of blushing again.

Just then, the clicking of heels close to their table caught their attention. Cas looked up and was surprised to see Meg, the singer.

"Dean Winchester. How the hell are you?"

Dean grinned wolfishly at her. "Meg. As I live and breathe. I'm getting by as always. Great show, by the way."

Cas nodded his agreement. "You were outstanding." She tilted her head at him and smiled.

"Thanks. Who's your friend, Dean?" She asked without taking her eyes off Cas.

"This is Castiel. He's a new associate."

"Ah. Roped another one in? How'd you get mixed up with this guy, cutie pie?" She drawled, reaching over to play with the cuff of his shirt sleeve.

"I, uh-

"Cas here just fell into it. Couldn't resist me, couldja Cas?" Dean grinned at an embarrassed Cas and then back at Meg. "Give him some breathing room, Meg."

"Fine, fine. I gotta go anyway. You boys be careful now. And have a good night." She waved flirtatiously at Cas and walked away, Dean narrowing his eyes at her as she passed him.

"Thank you," he breathed. Dean laughed.

"Don't sweat it. Meg's no tramp, but she likes to lay it on a little thick with the flirting sometimes. Messes with people."

"She's effective," Cas said to himself. Dean drew his mouth tight and rolled his eyes. "You want another drink?"

"Oh, no, I really shouldn't-

"Tomorrow's Saturday; where you gotta be?"

He had a good point, and any bad feelings Cas had about breaking the law was washed down with gin. They laughed and talked, and Dean managed to get Cas out on the floor one more time before the tavern started to empty. Dean, as it turns out, could hold his alcohol much better than Cas; the accountant stumbled a bit on the way back to Dean's car, thought the taller man seemed perfectly fine. He snickered at his companion several times.

"You have fun, Cas?"

"Y-yes," Cas hiccupped.

"Great. Let's get you home, huh?"

The drive was quiet except for Cas's occasional groans of regret at having gotten drunk. Dean busted out laughing.

"You're not drunk, man. Just tipsy. The hangover shouldn't be too bad." Cas mumbled something tiredly. When they pulled up to Cas's apartment building, Dean got out to help Cas out of the car and up the steps to his door.

"Thank you, Dean. That was…fun." Dean smiled brightly.

"I'm glad. You need to do it more."

"You're…interesting to be around." Dean made an amused sound.

"Thanks, Cas. You too." Dean noticed Cas's rumpled collar and without thinking, reached out to straighten it. Cas tensed.

"Are you afraid of me, Cas?" Dean asked quietly.

"No, sir," Cas whispered.

"Castiel. You've got to look people in the eye when they're talking to you. And it's _Dean_, dammit." He leaned one hand on the stone wall behind Cas, and slid the other hand under Cas's chin to tilt his head up. Cas could feel his face redden; his heart raced, quick and sporadic as a rabbit's. Slowly, he met Dean's stare. Curious, deep green orbs looked back at him. There was a rawness in Dean's eyes right now that Cas had never seen before, and couldn't place.

"No, Dean. I'm not afraid of you," he pushed out, surprised at his own sureness.

"Good," Dean breathed. "Good."

When Dean leaned in, the scent of his cologne filled Cas and made him close his eyes. Dean's commanding presence looming over him was not intimidating but welcome, thought the mobster had to wrap an arm around the accountant's waist when he felt Cas's knees go weak. Dean's mouth on his own was a new kind of overwhelming; the feeling set Cas's senses ablaze. Dean ran a thumb over Cas's cheekbone before sliding his hand to the back of Cas's neck. Cas rested his hands on Dean's biceps and became swept up in the sensations assaulting him.

When Dean broke it off, he leaned in for one more quick kiss before pulling back to look at Cas. The other man slowly opened his eyes, lips full. It was so beautiful Dean didn't know how to cut this off, but…

"Cas, you gonna be ok from here?"

Cas blinked a few times, trying to straighten out his brain.

"Oh, um. Yes. I can get up to my room."

Dean nodded, then started down the steps.

"Dean?" Cas said, a little too anxiously. Dean turned back to him.

"I'll see you soon, Cas. Promise. But I better jet." Cas's head was swimming, but when he opened the door to go inside he peeked over his shoulder one more time. Dean was on the driver's side, waiting to make sure Cas could get in. He grinned and tipped his hat at Cas and got in his car. Cas watched him go, dumbfounded. Once on the other side of the door, he pressed his forehead against the wood and closed his eyes.

_Oh, lord help me. What am I doing to myself?_


	4. Chapter 4

**A/ N: I had writer's block and this took forever to write, but here's chapter 4! Read and review, and as always, thank you:-)**

**Chapter 4 **

Blurry swirls of reds and browns greeted Cas as his eyes reluctantly opened. He blinked in confusion as the pattern of his living room rug came into focus. He also noticed that the coffee table and couch seemed much higher, and he groaned when he realized that he must have spent the whole night on the floor—and on his stomach, no less. Cas rolled over onto his back, his temples pounding in protest as he did so. He stared up at the ceiling and pieced together his memories of the night before. He recalled bright lights, music, an enchanting woman in red, drinking (ugh), and Dean-

_Oh. _

Cas rubbed his eyes. That's right. He'd kissed Dean last night. Or Dean had kissed him; yes, that sounded right. Cas closed his eyes and took a deep breath; he could almost smell Dean's cologne, as if the mobster were only inches away from him again. Cas sighed and slowly, painstakingly, got up from the floor, cringing at the popping sounds that came from his back, and at the stiffness in his neck and shoulders.

He yawned and sauntered to the kitchen, where he put on tea to boil and dozed at the table while he waited. He jumped slightly when the kettle whistled, and as he fixed a cup he stole a glance at the time. Seven o'clock. It was seven in the morning on a Saturday. Cas grumbled and rose from the table, leaving his mug. He took a few aspirin and went to his bedroom. He could let himself be unproductive this morning; his body was busy punishing him for coming in and crashing on the floor, and his bed just looked too inviting.

…

Cas awoke some four hours later feeling much better. The ache in his muscles was gone, and his head was infinitely less cloudy. He showered and had a proper breakfast, doing everything at a leisurely pace. It felt nice not to have to rush off somewhere, but the accountant found that he couldn't sit still. He didn't want to admit it, but Cas knew what it was. He longed to see Dean, to be near him again. Their kiss had intensified the already present pull that Cas felt towards the man, but at the same time he was very nervous. What had it meant? Why in the world had Dean done it? Now that Cas could think clearly, he almost couldn't believe it had actually happened. But…it had. Dean had leaned in close and kissed him full on the lips. Cas felt his lips, his face, everywhere Dean had touched heat up at the memory. He brushed his fingertips over his mouth and sighed. And hadn't he enjoyed it? Hadn't Cas, deep down, secretly dreamed of this very thing? Still feeling fidgety, Cas contemplated the things he could do: he could go to the office and get some work done; he could stay here and do some much needed things around the apartment; or he could go for a walk, and if that walk just happened to take him to the hideout…

No.

He would not appear clingy or naïve. After all, he had no idea what Dean thought of all this; the guy had had a few drinks himself, and maybe had let the alcohol act for him, though the thought made a cold lump form in the accountant's stomach. He ran a hand through his hair and leaned his head on the table. To the office, then. There was no way he was going to be able to putter around the house. He threw on some comfortable clothes and headed out the door, and was suddenly grateful that Dean had left when he had last night. It was easy enough for Logan's plain Model T to go unnoticed, but Cas had no idea how he would've explained Dean's Duesenberg. It surely would've caught someone's eye after a while. He strolled along, enjoying the pleasant day, but had to curse himself and double-back once when he realized he'd started walking in the direction of the hideout.

…

Dean didn't call or send a note the next day, nor did Logan come to whisk him away to Dean. It didn't happen the day after that, nor the next day after that, and to be frank it was starting to piss Cas off. He hated acting like a teenage girl getting her feelings hurt over a crush, but by Thursday Cas made up his mind to visit the hideout, bringing some fluffed up paperwork with him to go over with Chuck as an excuse. So after work on Thursday, Cas got on a bus that let him off close enough to the hideout to walk the rest of the way. He had been preparing himself all day, but the determination started to wear off as the building came into view; it was completely gone when he got into the front room and met Adam and Logan shooting pool. They both looked up, surprised.

"Logan. Adam. Hello."

Logan nodded to him and then lost interest, but Adam continued to eye him.

"What are you doing here? Dean didn't call for you."

"No, he didn't, but I don't see how that's your business," Cas snapped, losing his patience with Milligan's attitude towards him. He turned away before Adam could reply and before he could see the amused look on Logan's face.

He found Dean on the phone in his office. He looked up and did a double-take when he saw Cas in the doorway, but Cas still saw the slightly smug and knowing glint in his eye. He hung up the phone and looked up at Cas, smiling slightly. He leaned back in his chair and hooked his hands behind his head.

"Cas. What a nice surprise. What can I do for you?" The accountant licked his lips.

_Oh, nothing. I just wanted to see you. _

"I just…wanted to see if you needed anything, if everything was ok. You haven't contacted me since that big deal you said you worked out." Dean looked Cas up and down, considering him. He hummed and got up, coming around to the front of the desk. Cas pursed his lips.

"Nah. That's not it."

"Wh-what?" Cas stammered.

Dean closed the door and crossed his arms over his chest.

"You do not enjoy coming here. I find it hard to believe you just wanted to pop in out of genuine interest or concern. As long as we're leaving you alone, what do you care?"

Cas squeezed his eyes shut and groaned inwardly. So there went his excuse; Dean saw right through that bull crap. Now what? Cas's brain struggled to come up with something, but when he opened his eyes to face Dean again, the other man still had a small smile on his face, but those damn jade green eyes were set on him, serious and expectant. Cas couldn't help it.

"I guess I just wanted to see you, ok?" He gritted, splaying his hands out in frustrated resignation. He braced himself for whatever was to come; ridicule, anger, rejection, or any other soul crushing thing Dean would heap on him now. He was absolutely floored when Dean took the few steps to close the distance between them.

"There," Dean mumbled. "Was that so hard?"

Before Cas could muster up any kind of response, Dean reached out, cupped the side of his face and neck, and brought their lips together. Cas made a slight noise of surprise, but was resolute not to look like an idiot this time. Now, he was completely sober and could return the affection with equal eagerness. When they parted, both slightly breathless, Dean leaned down to press his forehead to Cas's. They stayed like that until Dean broke the silence.

"So it wasn't just the booze talking. Interesting," he lamented. "And good."

"Then why didn't you…?" Cas trailed off as Dean straightened back up.

"Why didn't I come for you again?" He gently suggested. Cas swallowed and nodded.

"Cas, when I kissed you it was mostly out of curiosity and impulse; but I realized that you'd had more to drink than I thought. We do have to work together, and considering your particular situation with us, I thought you'd prefer as little involvement and complication as possible."

Dean shrugged. "I figured I was doing you a favor by pretending it didn't happen."

Cas shook his head. "No," he whispered. "I-you've crossed my mind quite a few times in the last couple of months."

"Likewise," Dean smiled, easy and pure, and Cas couldn't help but grin back. "So, uh, what now?" Cas asked, slight worry seeping into his voice. Dean looked up, mocking a "thinking hard" face. He glanced back down at Cas mischievously and placed his hands on the shorter man's forearms.

"What do you say me and you hang out a lot more often? Hm?" He said, gently starting to rub Cas's arms.

The accountant's heart skipped a beat. "But what about everyone else?" Dean shrugged. "They couldn't care less as long as it doesn't affect them. And even if they did give a rat's ass, they'll keep their mouths shut. One of the perks of being the boss," Dean smirked confidently. Cas nodded slowly. "And Milligan? And what about your brother?"

Dean waved it off with a nonchalant flip of his hand. "Adam? Adam'll get over it. And you let me worry about Sammy, kay? It's alright. I've got this. I've got you from now on if you'll have me." He pulled Cas a little closer. "So what do ya say?"

Cas hesitated, but then looked up to the intense, almost childlike hope of Dean's gaze and felt electricity go through him.

"In that case…I guess I say ok," he answered softly, breathing a small, incredulous chuckle as he met Dean's eyes. The mob boss grinned like the Cheshire Cat and captured Cas's mouth in another possessive kiss.

…

The next few weeks were nothing short of surreal for Cas. He often zoned out at work when the thought of how strange his life was struck him unexpectedly. A few times, he left his office or home to find Dean waiting for him in a thankfully discreet car; Cas would get in quickly, still careful of the nosy residents of his apartment building. They'd go eat, or go to one of Dean's many hang-outs. People regarded Cas with perplexed curiosity, not sure how what to make of the nerdy looking man Winchester had taken to. For the gang's part, Dean was mostly right. Cas occasionally got raised eyebrows from Logan and Chuck, and noticeable looks of disdain from Adam when they noticed the change in their leader and accountant's dynamic. It only took a few glacier-level glares from Dean to put an end to any unspoken protests, and soon Cas learned another harsh reality. Though no one treated him any different, he could sense the shift and read between the lines as well as anyone else: he could be one of the guys, or he could be the Boss's pet, moving up to Dean's untouchable level. Of course Cas should've known that gaining something as powerful, as frightening, and as spectacular as Dean's love always came at a price. But Cas had made his decision; and he had no desire to turn back.

…

As Cas's legitimate business grew, so in turn did Dean's name and gang. People who had previously only given him credence as Singer's protégé or as John Winchester's boy were now recognizing Dean as his own man with clout. Cas could see the effect on Dean and it made him happy to see the other man so proud of himself. It wasn't long before the moral line in Cas's brain became fuzzy, and he was rejoicing victories with the mob even as the police were trying to crack down on such activities. They were _Dean's_ victories, Cas told himself.

And then there came a time when Dean completely discarded all the tact and professionalism Cas had worked hard to set up around the others. They'd made a lot of money doing something Cas wasn't sure he wanted to know, and in his excitement Dean tightly embraced Cas, arms around his shoulders and back. He pressed the side of his face to Cas's so that his lips were right next to Cas's ear, quietly breathed a simple phrase into the accountant's ear: _I love you._

At that moment, Cas made another decision. He would do anything for Dean; do anything for Dean and follow him anywhere.


	5. Chapter 5

**Chapter 5! Thanks for sticking with me, and for the reviews and follows; you'd think I'd write more now that it's summertime and I actually have the time, but no; I only get lazier:P I'll try to update soon!**

Chapter 5

Cas had fully planned on coming in and taking it easy; it had been a particularly trying day at work, and he was looking forward to flopping down on his couch and curling up with a book. Once again, however, his plans were derailed by a familiar voice over his home telephone.

"Hey, you, what's up?" Dean chirped pleasantly enough, and Cas smiled faintly as he always did when he heard Dean's gravely baritone.

"Hello Dean. Nothing; I just arrived home."

"Swell, swell. Hey, listen; you got any plans for tonight?" Cas hesitated. He knew where this was going; the question was an annoying courtesy as far as Dean was concerned. The mobster might as well go ahead and say what his tone implied: _"I already have something in mind so you're gonna have to say yes."_

Cas sighed; on the other hand, as usual, there was nowhere he'd rather spend his free time than with Dean.

"No; I don't have anything to do. Why?"

"Me n' Sammy are goin' out to have a little fun, do some gambling. I haven't taken you to a casino yet, plus I hear a certain big fish from outta town likes to frequent this joint when he's here on business. I've only seen him myself in passing a few times."

Cas cringed; he lived in almost constant fear that they were all going to get busted one of these days, but Dean always laughed away the accountants worries and had a way of putting him at ease.

"Alright," he finally answered.

"Great! See you at six."

"Dean, wait!" Are you…are you coming in the Duesenburg?"

"Pft, of course. There's gonna be a lot of classy snobs there, Cas. I'm not rolling up in anything but my best. Give 'em something to talk about," he grumbled.

"Fine, fine; but can I meet you at the corner or something?" He was still wary of Dean coming to his home, especially in the big shiny show-car.

"Sure," Dean laughed. "Alright, I'll let you get ready-wear somthin' pretty for me, huh?" He added. Cas breathed a chuckle and rolled his eyes, picturing Dean's wolfish grin on the other end of the line.

"Yes, Dean." They hung up and Cas immediately went to his closet and frowned. The accountant owned few dress clothes; his wardrobe ranged from rare, lazy-day lounging wear to slacks and button-up work shirts. He dug until he emerged again with a beige church suit that Cas had forgotten he even owned. He'd brought it from Illinois thinking he'd keep up with going to church every Sunday, but he'd really slacked off without his mother's constant nagging about it. He smiled and ran his hand down the lapels. Shaking himself out of a memory, Cas sighed. It would have to do. Dean was wearing and driving his best on a night that was apparently important to him and he wanted Cas with him. Cas could at least give him his best also, even if his best smelled slightly of mothballs.

…

Cas waited patiently at the corner for Dean and Sam. He spotted the Duesenberg rounding a curve and again marveled at it. He smiled in greeting at Dean and climed in. The accountant put on his seatbelt and was just about to turn and speak to the Boss when Dean planted a brief but firm kiss on his lips. He pulled back and smirked at Cas's expression. Their gaze lasted until Cas heard someone shifting and clearing their throat in the back seat.

"Oh! Hello Sam; how are you?" Cas's cheeks had gone a deep scarlet and Dean chuckled as he pulled away from the curb.

"I'm good, Cas. You?"

"I am well. Where, uh…where are we going, exactly?"

"To a casino, sweetness; the best in town."

"I'm glad you're coming, Cas. As our financial advisor, please be on wallet-watch for Dean." Dean shot his brother a look in the mirror.

"Relax, _mom_. My self-control is just fine, and it's not like I'm taking money out of the group's fund. Lay off."

Cas also glanced up into the mirror and discreetly caught Sam's eye; he nodded, and the younger Winchester's mouth curved up slightly into a grateful smile.

…

They arrived at the casino and Cas saddled up next to Dean, feeling a bit intimidated by the hordes of people. He noticed the colorful women and snazzy men, and felt out of place once again. Dean eyed him.

"Relax, Cas," he leaned in and straightened Cas's tie, meeting the brunette's eyes as he smoothed the lapels down. "I'm sorry; I didn't want you to get all self-conscious. I forgot you don't much have a reason for the glam clothes. Your trench coat would've been fine, too. I think I like you the most in it, anyway," he said softly, smiling at Cas. Cas reached up to gently squeeze the hand still gripping his coat. Dean's green eyes shone, and sudden blaring music diverted his attention to the casino.

"Shall we?" He inquired to both Cas and Sam, the latter having been scoping the crowd. The three of them started off towards the building, and Sam leaned over to speak in a lower voice to Dean as they got closer to the crowds hanging out outside the casino.

"I don't see him or any of his crew. He must be inside."

"If he's even here," Dean amended. He then checked behind him to make sure they hadn't lost Cas.

"Hey, stick with me. People here will get real friendly with you or Sam trying to get to me. Just be on your toes."

Cas nodded absently, too curious at this point. They stepped in the door and Cas almost gasped. The inside of the casino was vast and wide, with something going on in every inch of the place. Cigar girls and waitresses with drinks bounced around; machines were lit up, with a person at nearly every one of them, tense and anxious. Someone somewhere jumped up and whooped joyously, walking away from a table with a wad of cash. Cas took a moment to take it all in before Dean pressed a hand to the small of his back and gently guided him through the crowd. Cas people-watched and studied the various games with interest. His blood was rushing just watching them; the accountant could only imagine playing one.

"Here," Dean said, suddenly halting. "Black-jack's a good place to start. I can see most of the casino from here. Sam, you gonna go off?"

"Yeah. I'll let you know if I see him. Don't gamble away the car," he mumbled, only half-serious. Cas watched him disappear into the crowd and then turned back to Dean. He took a place at the black-jack table and patted an empy place next to him.

"Get in on this, Cas."

"Oh, I don'think so; it's been years since I've played cards, and never at a casino for money." Dean shrugged.

"Black-jack's easy, and you don't gotta bet a whole lot. Look, I'll front you some to get you started." Cas studied that cards that had been quickly passed out by the seasoned dealer. It was starting to come back to him, vaguely, and a good thing too since Dean was not allowed to whisper any tips or help him. They were technically playing against each other, after all, and Dean's competitive side often took precedence. Cas could see it now in the way Dean's face went completely blank and his posture became more rigid. He did, however, glance over and give Cas an encouraging wink before they got started.

It turns out that Cas remembered more than he had originally thought; he eventually backed away from the table and refused another hand after he'd won enough to cover the money Dean had loaned him and then some. He then remembered Sam's concerns and gave Dean's shoulder a gentle squeeze when it looked like the other man was about to go in again. Dean rose and gazed at him, bewildered. The look on his face matched the others at the table, all of whom had underestimated the quiet man, though Dean's eyes held more awe and pride.

"Cas, damn. When were you gonna tell me you were a hustler?" He asked mischievously.

Cas's eyes widened. "I'm not! My father taught me and my brothers how to play. I guess I forgot how good I was at it," he shrugged, remembering his father's lessons despite his mother's disapproval.

"Well, let's see what else you're good at. How 'bout we throw some dice?" Cas squinted up at him.

"I definitely don't know how to throw dice. But I'll come watch you and learn."

Dean led him up a short flight of polished wooden stairs to another level of the casino. They were offered a drink and Cas was surprised when Dean refused.

"Maybe later. I need to be clear headed, at least for a while tonight." He studied Cas and bit back a teasing chuckle.

"You, too. I've seen how you handle your liquor." Cas meant to glare at him but just blushed instead. "Do not worry; I have no plans to drink tonight, or possibly ever again," he mumbled, embarrassed at the memory of himself stumbling around with Dean.

"Hey, a little good came out of it, huh?" Dean said, raising his eyebrows. Cas smiled warmly.

"Yes, there's that," he amended. Dean hummed and turned to head to a nearby Craps table. Cas glanced over at the bar.

"I'm going to get a Coke, Dean. Be right there."

Cas leaned against the bar's counter as he waited, trying to stay out of the way. He didn't notice the slim figure that slid up to him until she spoke.

"Well, well, look who's here."

Cas whirled around and blinked.

"Meg? What are you doing here?"

"I come here all the time; the question is what are _you_ doing here?"

Cas looked over to the bartender, willing him to hurry with his soda.

"I'm, uh, here with Dean."

Meg quirked an eyebrow and gave him a slow, blood red grin. "My, he's managed to corrupt you but fast."

Cas considered her, wondering how much she knew or suspected. "He's my boss. I'm here for financial consulting."

Meg breathed a short laugh. "Sweetheart. Any idiot could tell he's sweet on you. And if my intuition is correct, and it usually is, the feeling is mutual." Cas was surprised and slightly alarmed that it was that obvious, but he refused to let her see. He gave her an expectant "and what of it?" look.

"Hey, good for you two," She responded, taking a sip of a fruity-looking drink. He eyed her dubiously.

"You won't spread it around?" Dean didn't seem to care who knew, but Cas was a bit more conservative. He was absolutely smitten with Dean, but with all due respect, the mobster wasn't the one with a legal, respectable business and squeaky-clean reputation to lose. Meg shrugged. "What do I care? It ain't none of my business."

Cas relaxed and offered her a small smile. "Thank you. Will you be performing tonight, Meg?"

She shook her head. "Nah. I'm just hanging out tonight. Toodles." She left and Cas turned back to the counter to see his Coke waiting in front of him. He made his way back to Dean, anxious to see how his game (and money) was going. He inwardly groaned when he saw Dean leaning on the edge of the table, brow wrinkled and shoulders hunched.

"Dean?"

Dean glanced up in acknowledgement. "Hey. It ain't goin' so great," he growled.

"I can see that. Should we move on?" Dean shook his head. "Nope. Give me a few more goes at it."

Sam came up behind Cas. "Hey, Cas. How's he doing?"

Cas shook his head. "He did okay at black-jack. It's not going as well here."

"Cas was freakin' _fantastic_, Sam. You should've seen him," Dean craned his neck and smiled back at Cas. Sam raised his eyebrows.

"Really?" Cas nodded, pride slipping into his grin.

"Good for you, man!" Sam said, slapping Cas on the back.

"Thank you. How have you fared so far, Sam?" The taller man shrugged.

"All right, I guess. Broke even once and then pocketed some."

"Goddammit!" Dean exclaimed as the other players collected another pile of cash.

"Bobby would absolutely kill him," Sam muttered to Cas.

"The hell was that, Sammy? You got something you wanna say to me?" Dean turned to face him, jaw tight. Sam held up his hands.

"Nothing, man. Just…maybe reel it in?" Dean held his gaze and then turned to Cas.

"C'mere, Cas." The accountant walked up to him. Dean put the dice in his hands.

"You do it." Cas blinked.

"Dean, no. I barely have the gist of this game; I'm not ready to try and win money."

Dean waved him off. "You can't possibly do any worse than me. Try." Cas glanced back at Sam, who shrugged helplessly.

"Ok," he sighed, focusing.

He threw the dice and instantly knew it wasn't good. Dean cursed quietly amidst the cheers that arose.

"Again, Winchester, come on; one more time. You've almost bought me a new car!" One man shouted.

Dean glared at him and gripped Cas's shoulders. "Alright, ok. One more time; ok? Just one more time," he said pointedly when it looked like Sam was going to protest.

"Double or nothing." Cas could hear Sam groan clap his hand over his face.

"Dean," Cas hissed. "Are you insane?"

"No. Look, I'll help you. I'm right here."

He wrapped his arms around Cas from behind, closing his hands over Cas's. Cas drew in a quick breath; there was that cologne again, and the comforting but sure pressure of Dean's tight grip. Other players and bystanders snickered and made snarky comments before a look from Dean silenced them.

"Luck be my blue-eyed accountant," he whispered, and Cas could feel Dean's warm breathe on his cheek, making the hair on the back of his neck stand up. He nodded stiffly and Dean shook Cas's hands in his own, jostling the dice. Cas held his breathe as Dean let go and released the dice from Cas's numb hands.

They landed and before Cas could read them himself, Dean was squeezing him tightly from behind, rocking him roughly and shouting right next to his ear. He placed a quick kiss to Cas's neck before releasing him and going to collect what was his.

Cas followed him and peeked around Dean at the dice. He'd guessed they'd won, but Cas wanted to see it. He breathed a sigh of relief and turned to Sam. He had clasped his hands behind his head and was standing stock-still in the same place, shaking his head. He finally managed an "Oh my God."

Dean came back to them, ignoring the grumbles and protests of disbelief from the others. He was grinning from ear to ear, eyes practically dancing. He saw Cas smiling contentedly at Dean's happiness and pulled the other man to him again.

"I knew you could do it!" He said, almost breathless.

Cas returned the embrace. "You did it, Dean. You gave me the confidence but pretty much did it yourself."

"No, man, wow; I mean, I just…

Dean stiffened and abruptly trailed off. His eyes seemed to home in on something specific over Cas's shoulder. Cas pulled back and studied his face, confused; he looked down over the rail to the level below them. Sam had gotten quiet as well, and Cas tried to follow their gaze. Dean reached over and lightly gripped Sam's elbow.

"It's him," and Sam nodded curtly in agreement.

Cas turned his face to Dean's. "Dean? Who?"

Dean pointed to a man in a black pinstriped suit with a red undershirt and black tie, holding a cocktail and surrounded by people.

"There he is. That's Crowley."

…

**A/N: I have a very loose understanding about Casino games and gambling, so I apologize for any mistakes. You people are the best, thanks for reading!**


	6. Chapter 6

**A/N: Welp, here's chapter 6! Thanks for reading, hope you enjoy it!:-)**

Chapter 6

"Is this…is this Crowley person the one we came here for?" Cas inquired as the three of them descended the stairs.

"Yes," Sam answered. "He and Bobby were about to rake in some serious bucks, but Bobby got sick and Crowley pulled out and fell off our radar for the most part. A deal with him would do wonders, to put it mildly."

"Business with Crowley would catapult us to the top, Cas." Dean further explained. "I've been waiting for the perfect moment to talk to the guy, and I think we're finally there." Dean looked down at himself and smoothed his hair; Cas could tell he was going into "savvy businessman" mode and knew to leave the mobster alone. He hung back when they got to the group of people circling Crowley, leaving him to the much more experienced brothers.

"Mr. Crowley," Dean said, planting himself in front of their target. Cas shifted around and peeked around other people in order to see the center of the group.

The man turned to them and raised his eyebrows.

"Yes? What can I do for you gents?" Came a British-accented, bored voice.

"I'm Dean Winchester; this is my brother Sam."

The younger Winchester nodded slightly in greeting.

"You may not remember us, but a while back you almost partnered with our—

"Wait, Winchester, you said? You're not Bobby Singer's boys, are you?" Crowley interrupted, suddenly interested.

"Well, yeah," Dean said, now thrown off.

"How about that?!" He turned to the others around him and spoke.

"Listen up, folks. It is with my deepest regrets that I leave you lot for right now. Ta, until next time." He watched as they dispersed, waiting until they were mostly out of earshot to mutter under his breath.

"Vultures and arse-kissers, every one." He then turned his attention back to the Winchesters. "Well now, this is a surprise. Let's chat, shall we?" Crowley gestured with his hand to a table. Sam and Dean followed, bewildered. This was not how they had pictured the introduction to go, and Dean had to regain his footing.

"Oh, uh, Mr. Crowley. This is our accountant, Castiel." Dean motioned for Cas to come closer. Cas held out his hand awkwardly, and Crowley shook it.

"Nice to, ah, meet you."

Crowley studied him and nodded. "So. Bobby Singer. How is the old codger?" He asked as they all sat down. Sam glanced over at Dean; the latter had tensed slightly at the mention of Bobby.

"He's…not well," Sam answered.

"Oh? Still?"

"Yes, sir. He's hanging in there, though."

Crowley hummed. "Sorry to hear that. Tell him I asked after him, yeah?" Sam nodded and Dean cleared his throat.

"That's actually why we wanted to see you tonight, sir. You were close to a partnership with Bobby when he got sick. "We want to see if you'd be willing to reopen that discussion." Crowley's eyebrows went up. "Are you boys acting in his place, then?"

Dean shook his head. "No. I basically run the business now, and have been since Bobby stepped back. I'm acting on my own interests."

Crowley took a sip of his drink and stared down at it thoughtfully. "You do realize that a man in my position can't afford to just make deals all willy-nilly, right?"

"I understand. And we are willing to do whatever it takes to prove to you that we're up for it."

"How many people you got working for you right now?"

"Five in my core group, counting Sam."

Cas cringed slightly. Dean stated the number with all the confidence in the world, but he knew that gang membership was the Boss's main weakness. Dean sensed Crowley's hesitation.

"But you will never find five more loyal, hardworking guys. They've proven it to me time and time again. And," he added, throwing a glance at Cas, "We have the best accountant in Boston."

Crowley eyed him with a cool, detached gaze, which he then shifted over to Cas. The accountant tried to keep his face neutral, but he could feel his pulse quicken at the other man's hard eyes.

"Alright. Let's do this, fellas; you pal around with me tonight. We talk, get to know each other's personalities a bit, play the room. And I'll be thinking about it. What do you say?"

Dean shrugged. "Fine with me."

"Fantastic! You up for some pool?" Dean and Sam said yes, and Dean saddled up to Crowley. Sam and Cas followed behind.

"Sam? What exactly is going on?"

"Crowley is feeling us out." Cas nodded, eyebrows scrunched together. They made the rounds in the casino until they came to the Poker table. Crowley invited Dean to sit down.

"Fancy some Poker, Dean?" Crowley folded his hands on the table and leaned forward. "You know, you can tell a lot about a man by the way he plays Poker. I wonder what you're going to tell me, hmm?" He grinned wickedly at Dean, who kept his gaze steady and unwavering.

Crowley was good. Much better than Dean had anticipated, and as the game dragged on Dean gradually became more nervous. He wanted to win. But more importantly, he needed to let Crowley know he was unshakeable. Crowley was too, apparently; he had a statue-like Poker face that gave nothing away—at least not that Dean could see, but Cas had barely taken his eyes off the Brit. When it looked like Dean was in trouble and a small, smug smirk twitched at the corners of Crowley's mouth, Cas suddenly leaned down to Dean.

"Dean?"

"Hm? Geez, Cas, kinda busy right now," Dean hissed lowly.

"But Dean, he's bluffing."

The mob boss went rigid but kept his deadpan expression. He motioned Cas down lower.

"What are you talking about?"

"Crowley is bluffing. Trust me, Dean. He's got a tell."

Dean glanced at Crowley, who was looking at him expectantly. "Cas, don't screw with me on this. Are you absolutely sure?" Cas licked his lips.

"Yes. Call his bluff." Sam looked anxious, but Cas simply nodded to him reassuringly.

Dean straightened up and put in another poker chip.

"Raise." He said confidently.

Something similar to surprise and maybe some anger flickered in the other man's eyes, and then it was gone. The look was replaced by amusement.

"Well, bloody hell. You got me." Cas let out a sigh of relief and Crowley stood to shake Dean's hand. "Damn good game. Thought for sure I had you," he said, looking at Cas. Dean shrugged. "You were good, too." Crowley studied all three of them for several minutes, as if thinking.

"I actually do have to go now. But…yes. You'll be hearing from me, Dean." Sam and Dean exchanged a look, and Cas couldn't help but notice that he looked like an excited little kid. They all shook hands with Crowley and then headed to the car. Once in, Dean grinned broadly and smacked the steering wheel.

"Yes! Holy shit, Sammy. How about that?"

"Awesome, Dean. Just great. I was worried, though, there for a little while."

"Nah; I wasn't. I knew we had it." Dean said, shaking his head as he started the Duesenberg.

"Would he really not have wanted to deal with you if you'd lost one poker game, Dean?" Cas asked incredulously.

"It's possible. Crowley respects guys that can hold their own in a card game. Plus, he doesn't know us very well and I wanted to make an impression. And we made one; thanks again in big part to you, Cas," Dean added softly. He found Cas's eyes and held them for a few moments; Cas could practically feel the affection and gratefulness radiating from those green depths, and he was content-deep and complete.

They pulled away from the curb, Dean and Sam talking seriously the rest of the way about their new situation. Cas half-listened, instead looking out the window and daydreaming or thinking about his own business. He was confused, though, when they dropped Sam off at his place first. Sam patted Cas on the shoulder and told him to have a good night. Dean's light and slightly mischievous, "We will!" earned an eye-roll from Sam and Cas flushed, though he wasn't entirely sure why.

"Dean?"

"We're going back to my place, Cas. Pop open a bottle of wine. And I've got something there for you."

Cas shifted in his seat. He and Dean didn't get to be alone very often, or for a long time, due to Dean respecting Cas's desire to keep their relationship on the down-low and the two men's schedules. But it seemed that that's what Dean had on his mind.

Dean's flat (the few times Cas had been in it) always amazed him. It was quite large, with a fun, swanky feel to it. Definitely a bachelor pad.

Dean closed the door behind them and raked his eyes over Cas's body. "Make yourself comfortable." Cas smirked and sat down on the couch. Dean came back with the bottle of wine and two glasses. He poured them some and raised his glass.

"To you, for saving my ass again." Cas snorted lightly.

"Dean, I did very little. You and Sam did the talking."

"Couldn't have done it without ya though, Cas. You're amazing," he whispered. Cas's eyes softened and he smiled at Dean. The other man abruptly got up and went to his room. Cas wrinkled his brow and twisted around on the couch. Dean came back out, holding a small box.

"I got you something. Just an extra thanks for everything."

Cas gave him a quizzical look and opened the box.

"Dean," he said breathlessly. "This…this is a Rolex. I can't take this, it's too expensive. It's too mu-

Cas's protests were silenced by Dean bowing to seal his mouth over the accountant's. Cas broke it off when he felt Dean take hold of his wrist. Dean took the watch from its case and snapped it around Cas's wrist.

"There. Perfect. It looks great on you."

Cas gently fingered the beautiful watch, brushing his fingertips over the ridges of the band, and then gently over the glass face. He looked back up at Dean, who was grinning. His green eyes shone brightly, happy that Cas was pleased with the gift. The brown headed man was speechless, so he thanked Dean the only way he could think of at the moment. He reached up and wrapped his arms around the mob boss's neck, pulling him in for another kiss, this one much deeper and full of devotion and thanks on both their parts. Dean gripped Cas's waist tightly, the two only pulling away, slightly breathless, when the kiss threatened to become smothering. Cas's mouth was full and flushed, and Dean's gaze immediately flickered to it, and then back up to Cas's blue depths. Dean licked his lips.

"Cas," he said in a low growl, and Cas shivered. He closed his eyes and nuzzled Dean's cheek.

"Hmm?"

Dean leaned in next to his ear. "You're goddamn beautiful."

…

Sunlight pierced through the curtains in Dean's room. Cas grumbled and rolled over onto his back, eyes reluctantly fighting sleep and opening. He blinked a few times and sighed. He loved Dean's bed. It was big, fluffy and ridiculously comfortable, with soft pillows and smooth sheets. The complete opposite of Cas's own modest, smaller bed at home, and the accountant hated leaving it. But all those things still weren't what made it the best. The best thing did not have his arms wrapped firmly around Cas's waist, like normal; Dean was instead in the living room, talking in low tones to someone on the phone. Cas was about to close his eyes again when he heard Dean hang up. He appeared in the doorway and smiled at Cas.

"Mornin'."

"Morning," Cas returned the lazy grin. He loved seeing Dean like this; so relaxed, so natural in just a white t-shirt, boxers and bedhead. Dean sauntered over and flopped down on the bed, on his knees. Cas reached up and ran a hand through his uncombed, honey-brown locks.

"Was that something to do with Crowley?" Cas asked, curiosity getting the best of him.

"Nope," Dean said, leaning down to kiss Cas's neck.

"That was Bobby. Sam must've talked to him already this morning. He's over the moon, says it'd be damn great to get Crowley."

Cas nodded. He wanted to ask about Bobby, to know more about the mysterious man Sam and Dean apparently idolized. But he also hated to cast a somber shadow over the lighthearted, playful mood this morning, so he kept is mouth shut and wrapped and arm around Dean when the latter laid his head down on his shoulder, face resting in the crook of his neck.

"What time is it?" Cas asked as an afterthought.

"You've got a watch, you tell me." Cas excitedly reached for his new gift sitting on the nightstand; he wasn't used to having a wristwatch and he'd forgotten about it. Now, again, he marveled at its silver beauty. The hands read 10:30am. Cas grumbled again. "I should get up."

"Why?" Dean chuckled. "Why do you always feel like you have to be doing something?"

Cas shrugged. "I don't know. I just don't like to be idle for too long. I guess it comes from working so much get my business started. I get anxious if I'm not being productive."

Dean laughed at him. "I thought hanging around me would change some of that. You got something you really have to do?"

"No," Cas admitted. He drew in a quick breath of surprise when Dean pulled on him, rolling himself over on his back so that Cas was on top of him.

"Good. Stay, then." Cas ran his hands over Dean's shoulders and chest, finally giving in.

"Of course," he conceded. He bent down to lay his head on Dean's chest, closing his eyes and sighing contentedly. The birds chirped outside, but Cas could tell by Dean's steady breathing that he was dozing again. Cas yawned, not far behind him.

…

Later that evening, Cas did actually have to go despite Dean's protests. He had work the next day, and had several things he wanted to do at home beforehand. Dean mentioned that the group was going to be meeting Monday afternoon to go over a new game plan, and he wanted Cas to be there. The accountant leaned slightly upward for a good-night kiss before heading home, Dean watching him from the doorway, a faint smile on his face.

…

Cas shoved his hands in his pockets as he walked. He'd gotten off the bus a little further away from home than normal; he liked this part of town at this time of night, and wanted to take in the street musicians and poets. As a saxophone blared out a jazzy tune in the distance, Cas noticed a new clothing store. It was a modest looking little place, but the men's clothes on display had caught his eye. He chewed his lower lip and patted his pocket where his wallet was tucked. He thought of Dean, then, and how put-together and confident the man always seemed to look. Without further hesitation, Cas slipped into the shop.

…

Cas hummed as he got ready for work the next day. He straightened the tie on his new light blue suit and slicked back his hair before stepping back to examine himself in the bathroom mirror. He nodded, satisfied with his reflection. As he passed his dresser, he grabbed what he considered his new crowning jewel. He put on Dean's watch and left for the office.

Cas couldn't help but feel a bit vain as he strolled down the street. Men actually made eye contact, and women giggled and looked away, some of them even giving him a not-so-subtle once over. He was whistling when he got to his building, and could hear Sally moving around in the front.

"Good morning, mistah Novak. A file was dropped off for you and—

Sally blinked. "Oh! Well; you look…very handsome this morning, sir, if you don't mind me saying."

Cas beamed at her, his confidence soaring. "Thank you, Sally. You were saying?"

"Right, right. I'll go get that file for you, and a cup of coffee."

Cas tipped his hat to her in a mock-dramatic gesture, and Sally blushed and scurried away. Cas hung up his hat and settled down at his desk to start the day.

…

That afternoon found Cas stumbling into the hideout almost half an hour later than the time Dean had appointed. He made his way to the back and sheepishly slipped into the room, hoping to go unnoticed. No such luck, as the Boss himself stopped in the middle of his sentence and quirked an eyebrow at him, tilting his head slightly at the new suit. Everyone turned around and Cas cringed. Milligan scoffed.

"Teacher's pet, dropping in whenever he feels like it. I told you it was only a matter of time before—

"Adam. Kindly stuff it, will ya?" Dean reprimanded. The accountant held up his hands.

"I apologize, everyone. I got held up at work."

"What's more important than this?" The blonde snapped.

"Milligan, what the _hell_ did I just say?!"

"I do have an actual life to maintain outside of this business," Cas retorted through gritted teeth. Chuck continued to stare uncomfortably into his coffee mug; Logan leaned back in his chair, crossed is arms over his chest, and watched the show with growing interest and humor.

Sam, from his place leaning against the wall behind Dean, opened his mouth to say something but then though better of it. Dean managed to make everyone jump by slamming his palms down on the table.

"Hey! Both of you! I shouldn't have to tell any of you how to act. Cas, just take a seat somewhere, one of us'll fill you in on what you missed later. Adam—mind your own business. If something is a problem, I'll let you know. Now. As I was saying."

Cas didn't fail to catch the glacier-level glare that Adam snuck in; it was akin to the look he had in his eyes the night he nearly shot Cas in the streets, but the brunette wasn't afraid. He tightened his jaw and met Milligan's hard gaze with equal vehemence; Milligan was the first to break contact, prying away to turn his attention back to Dean. If anyone else felt the tension they made no comment.

…

Logan and Adam were to gather as much intel on Crowley's cronies as they could. Dean dismissed everyone else when he got to their specific duties; Cas stopped to speak to Chuck and set up a time to talk about financial matters. He was a little surprised to see Sam approaching him as he and Chuck wrapped it up.

"Hey, Cas; you got a minute?"

Chuck gave Cas a look and an encouraging punch on the arm.

"Whatever that's about, good luck," he whispered to the accountant. Cas rolled his eyes and turned to Sam.

"Of course, Sam. What do you need?"

Sam pursed his lips and studied Cas, seeming conflicted about something. When his eyes rested on the Rolex on Cas's wrist, he swallowed.

"Why don't you let me give you a ride home, Cas?"

Cas was about to politely decline, but something about the way Sam was acting stopped him. The younger Winchester was as friendly as ever to the accountant, but it was clear he wanted to talk to Cas.

"Um, sure, Sam. I'd appreciate that."

Sam smiled. "Great. Dean, I'm taking Cas home." Dean glanced over at them and nodded curtly. Cas inwardly sighed; he hadn't meant to put Dean in an awkward position earlier, and he hoped the mobster wasn't angry with him. He reluctantly followed Sam to his car.

After they'd pulled out of the lot, Sam cleared his throat.

"So, Cas, I know it hasn't actually been said out loud, but…you and Dean." Cas felt his heart rate speed up. Had there been some misunderstanding? Surely Dean's brother…

"Relax, man. I know. Everyone knows."

Cas nodded and groaned. "Yes. What…exactly is it that you want to know, Sam?"

"Do you love him?"

The question caught Cas off guard and made him fidget, though not for lack of an answer. Cas knew the answer, and had for a while. "It's early, but…yes. I care for your brother very much, Sam." Sam nodded slowly.

"Ok. Why?"

Cas blinked. What a question. "Why? Well, he's strong; and brave. He's funny, and has an interesting and beautiful mind. He's a good man, despite what he wants the world to believe." A ghost of a smile appeared on Cas's lips. "He's…

"He's a murderer," Sam said softly but very matter of fact. Cas froze where he sat, breath hitching in his throat. Sam glanced over at him and shrugged a shoulder. "Sorry. It's true. If you love Dean, you gotta take him for what he is. And he has killed before, Cas. But I shouldn't have to tell you. You were there once. You do realize he almost killed you, right? That it wasn't love or his "beautiful mind" keeping him from snuffing you? That it was me?" Cas turned to Sam, a long buried curiosity bubbling up.

"Why'd you do that, by the way, Sam?"

Sam sighed. "I don't know, man. Part of me did think you'd be useful. Mostly, though…it's because those things you said were true. Dean's a good guy. Anyone who says different would certainly have a valid point, but in his own way, under these circumstances, Dean's more patient and soft-hearted than a mob boss has any right to be. Make no mistake, he'll kill if necessary. I've seen him do it. But I can tell it does something to him, even if the target really deserved it. I'm just afraid-I don't want him to become hard. I don't want him to be like Dad and Bobby. The more bodies to his name, the closer he is to that happening. That night you were dragged in, I don't know. I just felt this urge to step in—for both of you."

The silence after Sam's lamentation was palpable. Cas finally broke it.

"Well…for what it's worth now, Sam, thank you. I owe you my life." Sam waved him away good-naturedly. "Don't mention it."

"But I have to ask…why are you telling me all this?"

Sam chuckled, slightly grim, and said, "Look at you, Cas. You're starting to emulate him. And I see he's already buying you gifts." Cas instinctively fiddled with his watch.

"It's not that I care who Dean sleeps with Cas; it's just that, well, it's a bit more complicated when you're supposed to be working for him. It was starting to look like things were getting serious, though I gotta admit I kinda hoped you were just a fling and he'd get over you." Cas cut his eyes at Sam. He gave the accountant and apologetic look.

"Hey, I'm wrong, aren't I?" He responded defensively. "There were just some things I wanted to make sure you understand." Cas hesitated but decided to go forward as long as Sam was being generous with information.

"Sam…why does Dean not like to talk about Bobby very much?" Sam tightened his grip on the steering wheel and muttered under his breath about not even knowing where to start.

"Castiel…Bobby is all we've got. Been that way since Mom and Dad died. Dean is completely devoted to him, and he's part of the reason Dean even does what he does. But Bobby has standards; not quite as high and unforgiving as Dad, but the idea of disappointing either of them keeps Dean up at night. The thing is, though, Bobby's dying." Sam rubbed his eyes with one hand and Cas looked down at his lap.

"I figured as much. I'm very sorry."

"Yeah, and when he goes, which won't be long now, Dean'll have no one to turn to. He's got a good brain, and he's smart; picks up on things real fast. But there were things Dad didn't quite get to, and Dean's about to lose another father figure before he has a chance to say what needs saying."

Cas let the weight of Sam's words sink in before he continued. "Sam…forgive me, but you seem to be taking this well. Who was _your_ father figure?"

"Dean," Sam answered without hesitation. "Don't get me wrong, I love the old guy with all my heart and just because I'm expecting it doesn't mean I'm ready by any stretch of the imagination. But I'll have Dean when it's over. Dean won't turn to me with his problems; wants to be the tough guy. But I'll tell you, he's gonna need someone bad, Cas. We're here."

Cas blinked and whirled around to look out the passenger window. Sam put the car in park. "Look, Cas, I'm telling you all this for your benefit as much as Dean's. Trust me, I know he ain't perfect. He's stubborn and doesn't know how to do relationships. But on the rare occasion that he decides he really likes someone, he falls for 'em hard and usually gets burned. You seem different, and he's different with you, even with you guys meeting the crazy way you did. I just..don't want him hurt. And I don't want you hurt, either, or getting in over your head. I know Dean comes on pretty strong sometimes."

"Sam. I don't know what to say. I—thank you. I think."

Sam breathed a light chuckle. "No problem. Listen, I know I've given you a lot to chew on. I'll let you go on home. See you later."

Cas hopped out of the car and turned back to Sam.

"Have a good night, Sam."

"You too, Cas. Later."

He pulled away and Cas sat down on the stoop, resting his arms and head on his knees. He stayed like that until the landlord had to come ask if everything was alright.


	7. Chapter 7

**A/N: Writing when I should be working, again. A slightly timelier update to make up for that last month-long hiatus:P As always, your reviews are much appreciated and I thank you for reading!**

…

It had been a long time coming, that phone call. It'd been hanging over Cas since he'd met Dean, though the accountant didn't realize it until after. Of course, it had been hanging over the Winchesters for far longer-though as Sam said, expecting something doesn't always mean that you are ready for it; and Cas could tell by Dean's distant, hollow voice that evening that nothing in the world could've properly prepared him for the inevitable.

Cas had just gotten home; he was changing into more comfortable lounging clothes when the shrill ringing of the phone cut through the quiet apartment. Cas snatched it up and greeted the caller in his usual friendly way.

"Cas?"

Immediately, alarm bells went off.

"Yes? Of course it is, Dean."

"I—Sam's away with his new girl for a few days and can't get home until tomorrow. I finally got a hold of him but didn't know who else to call and-

"Dean," Cas gently interrupted the other man's rambling. "What is it? What's wrong?" There was a heavy pause that seemed to go on forever, and Cas can imagine Dean running a hand through his light locks, stopping at the back of his neck.

"Cas….Bobby died."

The accountant reached for a chair, suddenly needing to sit down. He closed his eyes.

"Oh, _Dean_. I'm sorry. I'm so, so sorry. When?"

"A few hours ago. They said he went in his sleep, and I...I wasn't here. I mean, I just talked to him a few days ago and _**goddammit**_ I wanted to be here when—

"Dean. Where are you right now?"

"Bobby's place. All the hospital people and most of his neighbors have already left and I'm here now."

"Are you far from me?"

"No."

"Come over," Cas said automatically.

"To your apartment? Cas…you sure?"

"Yes, Dean. You don't want to be alone right now, nor do you need to be. Plus, I want to be with you at a time like this." Dean hesitated but agreed. The accountant hung up and rubbed his eyes.

_He's gonna need someone _bad_, Cas._

Cas made sure he had extra pillows on the bed and comfortable blankets. He put fresh coffee on and then went outside to wait for Dean. He didn't have to wait long for two headlights to appear around the corner. When Dean got out, Cas bit back a small gasp. The mobster looked wiped out. His hair was mussed and his broad, usually set shoulders were slumped, and he moved slowly, painstakingly. When he saw Cas, he swallowed hard and made a small move as if he wanted to go reach for him but hesitated. The slight gesture was all Cas needed. He rushed Dean, reaching up to wrap Dean's neck and shoulders in his embrace. The Boss sighed deeply and bunched the back of Cas's shirt in his hands, burying his face in the accountant's shoulder. They stayed like that until Cas kissed the corner of Dean's mouth and spoke softly;

"Dean. Let's get inside." The other man nodded stiffly and the two went up to Cas's apartment. When the door was closed behind them, Dean asked:

"You're not worried about your neighbors talking?"

Cas shrugged it off. "Let them. Shame on them if they don't have enough going on in their own lives that mine is of interest."

Dean snorted lightly, a tiny ghost of a smile pulling at the corners of his lips.

"Sit down, Dean." Cas got them both a mug of warm coffee and sat down beside Dean, moving his hand to rub the back of Dean's neck.

"I think I knew. I think…I knew a few weeks ago that he was close. He'd been eating less, and sleeping more, but I thought he'd bounce back. That's what he usually does, for the past year he just kept fighting."

Cas remained silent, patiently waiting for Dean to say whatever he needed to say.

"I didn't thank him enough. He's been my dad since I was fifteen and I didn't fucking thank him." Dean's voice became heavy with restrained tears and he buried his face in his hands. Cas's heart ached.

"Dean…but you did. You thanked him by being the person you are today. He got to see you become a man. I'm sure that's all he needed." Dean's eyes were red-rimmed when he looked back up. Cas dragged his hand from Dean's neck to the side of his face, and Dean closed his eyes and leaned into the touch.

"God, what am I gonna do now?"

Cas stood. "It's late. Right now why don't you get some sleep? Thery'll be a lot to do for you and Sam tomorrow and you're gonna need some rest."

Dean didn't protest, instead allowing Cas to lead to way to his bedroom and peel away the layers of his clothing until Dean was in just his undershirt and boxers. The mobster breathed a deep sigh when his head hit the pillow; when Cas crawled in next to him, he shifted on his side to look at Dean. He looked so young now, so vulnerable and sad.

"Cas," Dean rasped.

"Hm?"

"It feels like I lost Dad again, only different. Worse, almost."

Cas moved closer until their noses were brushing against each other. "I know. I know, Dean. It'll be ok. I'm not going to leave you and neither is Sam." Dean's lips parted, about to say something, but he just flung an arm around Cas's waist and leaned into him. He was asleep soon, but Cas was awake for a while, rubbing circles on Dean's back with his hand. When he shifted to get more comfortable without waking Dean, Cas noticed a wet spot on the shoulder of his t-shirt. He looked back down to study Dean's face and gingerly wiped away the dampness from beneath the Boss's eyes with his thumb and kissed his hair before falling asleep himself.

…

Cas was up before Dean the next morning, making them both pancakes, bacon, and eggs. Dean and Sam had a tough few days ahead of them. Cas could at least make sure this one started off on a good note. He turned when he heard the sleeping shuffling of feet coming from his room. He smiled at Dean as the other man yawned and stretched.

"Hey, Dean. How are you this morning?"

"M'fine, Cas. I was just a little shocked last night. I'll be ok; Bobby was sick, and had been for a long time."

Cas nodded. Dean looked well-rested and less tense.

"Come eat something, Boss." Dean grinned and plopped down in a chair. His eyes wondered around as they ate.

"So…this is your place, huh?"

Cas looked down at his food, slightly embarrassed.

"Yes; I guess it was about time you saw it. I'm sorry, Dean. I was never ashamed of you, I just-

"Cas, it's fine," Dean chuckled. "I get it. We have a weird-ass relationship that requires some…_alternative_ solutions. Don't worry about it; I know you gotta be way more careful than me. I want you to be."

Cas met his eyes and smiled greatfully. "Thanks, Dean. So when did you say Sam is coming in?"

"Early this afternoon. I'm gonna hold off on arrangements until he gets back." Dean cringed a bit and Cas studied him.

"Should-do you want me to come with you? Or is this something you and Sam want to do by yourselves?"

"I'd like it if you came, Cas," Dean whispered.

Cas nodded and Dean went back to his plate of food. Cas got up to put his in the sink, letting a hand brush gently over Dean's shoulder as he passed him.

…

They met Sam in front of Bobby's. Cas could tell he'd come straight here and hadn't even stopped at home yet, judging by his wrinkled clothes. The accountant noticed how strained and tired the taller Winchester looked as he and Dean embraced. Cas stood back at a respectful distance, and held out a hand when Sam came up to him.

"Sam. I'm so sorry. How are you?" Sam took Cas's hand.

"Thanks, Cas. I'm ok, I guess. I shouldn't have left; he—

"Sam, c'mon. We had no reason to think this was going to happen yesterday. You can't put your life on hold; hell, remember back several months ago when they said he only had a few days? And the tough old buzzard told the doc to go screw himself and decided to live a while longer?"

Sam chuckled and Dean smiled wistfully.

"Well. I guess we got stuff to do."

Sam nodded and the three men set off. Throughout the day, neither Sam nor Dean paid much attention to Cas. The accountant stayed mainly in the background as they went about handling their surrogate father's affairs, which, thankfully, had been mostly laid out for them with little hassle, thanks to Bobby having the foresight to prepare for his own impending death. When they were picking out a casket at the funeral home—their last stop for the day—the mood became noticeably more melancholy and Cas noticed Sam swallowing a lump as Dean ran a hand over the heavy wooden oak of one of the caskets.

"Gettin' more real, huh?" Sam muttered. Dean nodded. Sam slumped his shoulders and continued to look around; Dean turned suddenly to search for Cas, slightly frantic for a moment before his eyes registered the accountant right behind him, every step of the way as he'd been this whole time. Cas smiled reassuringly at him, blue depths full of patience and support and love, and Dean felt the tightness in his chest loosen. Cas was there. His presence, though not always acknowledged, was felt none the less, a constant and comforting weight over him. Dean thanked him with what little expression he could muster in his own green orbs, and turned to catch up to Sam, Cas only a few steps behind.

…

The funeral would be tomorrow, no sappy memorial service or visitation per Bobby's request. Bury him and get it done with. Dean, Sam, and Cas stayed at Bobby's that night, packing and cleaning up what little possessions he kept in his final year. Cas helped where he could, and when they were done the three of them sat on the floor and Cas listened as the two men told stories and highlights of Singer's life. How he'd been feared by his enemies and respected by his employees; about his tumultuous relationship with John Winchester, and how he'd both respected and hated his former partner. And finally, how he'd been the first to step up when John was gunned down in front of his home, immediately taking in a scared Sam and an angry teenage Dean without a second thought. Cas had to admit that one could think whatever they wanted to think about the way of life and business that Bobby Singer had passed on to his boys; but it was clear by the blatant grief on their faces and the admiration in their eyes that, above all else, Dean and Sam were loved when they otherwise might not have been.

...

Cas wasn't sure when everyone fell asleep; he just knew that he woke up at midnight to Sam gently shaking his shoulder.

"Cas? Hey, Cas; why don't you go home, get some sleep?"

Cas rubbed his eyes and looked around. Dean had fallen asleep on the floor as well a few feet away.

"We'll be ok. You've done more than enough running around with us; Dean'll be fine, we'll both just stay here tonight."

"Y'sure?" Cas's sleep-ridden voice slurred. He hated to leave Dean, but then again his brother was here with him.

"Yep." Sam reached out a hand to help him up. He walked Cas out to the street, which was eerily noiseless this time of night. That's when Sam surprised Cas by leaning down to briefly embrace the shorter man.

"Thanks, Cas. Thank you for being here for him."

Cas nodded. "Sure, Sam. I meant what I said, you know; your brother means a great deal to me."

"I know. Sam goes for him where you're concerned, I could tell especially today. The funeral will be at 1:00pm tomorrow; Bobby wouldn't have wanted this, but Dean's place is gonna be open to everyone for a few hours afterward." Sam shrugged. "We still gotta play politics and let everyone come pay their respects somewhere."

"Alright. I'll come early to ride with you."

"Dean would like that—and I appreciate it." Cas gave Sam's shoulder and awkward pat.

"Again, Sam, I'm sorry for your loss." Sam grinned warmly and turned to go back inside. Cas yawned and headed home.

…

The funeral was brief but well-attended. Cas stayed behind Dean, hands behind his back, as he and Sam shook hands and accepted condolences, among them the gang. Dean embraced Adam and Chuck with sincerity and clasped Logan's hand. They hung around for a few minutes and then gradually dispersed to let the brothers pay attention to other guests. Cas blinked in surprise when Crowley made an appearance. He hadn't noticed him before.

"Dean; Sam. I'm so very sorry." The Brit went to each of them, firmly gripping their hands in both of his.

"Thank you, sir. He would've been honored to know you came."

"Of course. Nothing but good things to say for the ole' bloke. I hate to bring this up here, but when you're ready to talk, here's a number you can reach me at."

Dean blinked. "Oh! Well, thank you. We'll be in touch." Crowley nodded and sauntered off to his car. Dean shrugged.

"Well that was unexpected," he mumbled, flipping over Crowley's card.

"Good sign?" Sam asked.

"I guess so. Crowley doesn't seem like he gives away his contact information freely. We'll worry about it later, though," he sighed, glancing back at the fresh mound of earth behind them. Sam and Dean went to it, and Cas said a silent prayer for the man who'd raised Dean before making his way down the hill. He watched the brothers for a long time, until Dean threw an arm around Sam's shoulder and pulled him into a hug as they came down to meet Cas.

…

Weeks later, things seemed to be getting back to normal. They'd pretty much slipped back into their lives with ease, Dean and Sam able to move on at a quicker pace now that all the funeral hustle and bustle was done with. So Cas had no reason to suspect that this particular Tuesday would be any different. But he could sense something off the minute Sally knocked on his door with a perplexed expression.

"Sir? There's a rather handsome man here to see you; he doesn't have an appointment but says it's important that he catch you today before you leave."

Cas breathed an amused chuckle through his nose. "Well let's not keep this handsome gentleman waiting, Sally. Send him in."

Cas bent his head to quickly finish signing off on a few forms. He looked up when he heard the door shut.

"And what can I do for you, Mr.—

Cas stopped mid-sentence, nearly dropping his pen.

"Hello, Mr. Novak. Quite a nice set up you have here."

"Mr. Crowley. What, uh, what are you doing here?"

"Me? Oh, I just wanted to chat with the accountant Dean Winchester seemed to hold in such high regard. May I?" He asked, and Cas nodded and gestured to a chair. There was nothing overtly sinister, but months later, the accountant would look back on this moment in stunning hindsight and recognize it as the point where everything first started to go wrong.


	8. Chapter 8

**A/N: Ugh, I know, I know. It's been like, two months and I am SO SORRY!:-( My summer stuff has finally settled down and I can finally write now. So, here's chapter 8! Your patience and willingness to stick with this story is duly noted and greatly appreciated:-)**

Chapter 8

"You been here long? I mean, in Boston?"

Castiel shook his head. "No. Less than a year."

"Hm. Well I have to ask the obvious, how'd a bloke like you get tangled up with Dean Winchester?"

Cas licked his lips. He had no idea how much to tell this man, if anything. What if Crowley was trying to trick him, and something Cas said or did in this moment makes up the Brit's mind about a partnership with Dean? He decided to go with a variation of the truth.

"I got into some trouble and Dean offered me a way out," he stated simply. Crowley seemed to accept this.

"Just curious. So…upstanding citizen by day, mob accountant extraordinaire by night?"

Cas chuckled dryly. "Yes, something like that; I make it work."

"Good. That's good."

Crowley was silent then, and Cas was itching to check his watch. It would be easy to explain him away as a potential client, but Castiel still didn't like having the mobster in his office. The overlap between his two lives was making him increasingly uncomfortable the longer Crowley stayed. Plus, he was having dinner with Dean when he got off work and-

"Am I keeping you?"

"No!" Cas answered quickly. "I mean, I have time to talk. But…is there anything specific I can help you with?"

Crowley smirked. "To the point. I like that. Yes, as a matter of fact." The other man leaned back and pressed his hands together, touching them to his lips in thought. "As you probably know, your Boss and I may be on our way to some sort of partnership—sharing contacts, wheeling and dealing, the like. But I know for a fact that their finances went to shit when their uncle became ill, and that they're just starting to get back on their feet as a group, thanks at least a little bit to you. So tell me," Crowley said, leaning forward. "What am I getting myself into?"

Cas chewed his lip, feeling sweat starting to form along his hairline. He wished he'd gotten clear instruction on what to do should a situation like this ever present itself. As it was, he was on his own. He cleared his throat.

"I can tell you that I consider myself a very capable manager of other people's money, Mr. Crowley. Under mine and Chuck Shurley's supervision, the Winchester's financial standing—and in turn their standing as a respectable gang—has improved dramatically, as you've heard. Take from that what you will."

Cas felt confident in his answer, having phrased it in a way that revealed more about himself than Dean, yet still answered Crowley's question. Crowley drummed his fingers on his leg and nodded slowly. He stood and so did Cas.

"Right then. Sorry to have taken up your time. Hopefully we'll meet again soon. Oh, and Castiel—do me a favor and don't mention our chat to anyone, hmm? A smart man doesn't go into anything blindly, I'm just protecting myself. A rather insignificant thing to bring up, yeah?" Cas nodded hesitantly. He didn't feel good about it, but again there was the desire to make a good impression on Crowley for Dean's sake. They shook hands and Cas breathed a sigh of relief as he watched the man leave.

_That was odd._

He couldn't shake the uneasy feeling he had, and it stayed with him the whole way to the restaurant where he was to meet Dean. Should he tell him? It didn't feel right, keeping things from Dean. But Crowley hadn't said anything particularly life-changing, and Cas felt confident that he hadn't revealed anything that would concern Dean.

"Why the deep-thinking look?" the Boss chuckled, leaning down for a quick kiss. Cas smiled and studied Dean's face. He looked so relaxed and happy; Cas was reluctant to bring business into the time that was dedicated to just the two of them.

"Nothing," he said, perhaps more to convince himself.

"It's nothing."

Dean grinned and wrapped an arm around Cas as they went into the building.

…

Dean's first dealings with Crowley were, by their standards, pretty small. Bootlegging, to be exact—some of the purest and finest liquors Crowley could get. The goal was to get it here and sell it to some of the upscale clubs in the nice part of town as efficiently and low-key as possible. The very rich, Castiel discovered with some amusement, were not above being seized by the basic yearn for alcohol. All the money in the world could not fill the void that the thirst for the illegal but coveted booze caused, and in that aspect Boston's upper crust was no different than the rough and sketchy patrons of the seedy bars tucked away in the dark corners of the city.

Crowley would need Dean's help. The clubs were close to Dean's part of town, and his crew knew the back streets and basic directions better than Crowley's gang. Plus, Dean had friends on the loading docks and delivery trucks who owed him favors. It was a vital service that Crowley was quick to thank Dean for, first by giving him a huge cut of the profits, and then by sharing with Dean a few of his own contacts—most of whom had access to richer clientele that Dean would otherwise not know of. It was a significant act of trust and respect, and thought Dean retained the calm façade of professionalism, behind closed doors with Cas and Sam, he was as ecstatic as a little kid.

"Nah, man, this is small stuff; bootlegging is a good start but it's hardly the big time," Dean explained to Cas one evening in the latter's apartment. They were catching up with the books, Cas figuring out where to put the money that Dean and Crowley's latest excursion had raked in. The accountant could see how much it meant to Dean to not only be going up in life, but also to be able to pay his gang a fair cut. Not that any of them were on the verge of leaving—either out of loyalty or because they had nowhere to go—but it was embarrassing to Dean to only give his employees enough scrape by. They had lives and homes to maintain too, after all. Cas hummed thoughtfully.

"So what's next, then?"

Dean shrugged from his place on the couch. "I don't know. Lotta options. I want to work a bit more with Crowley on what _he's_ got lined up before I start pushing my own ideas." Cas nodded and turned back to the folders spread out on the floor in front of him. To his relief, Crowley had not tried to personally contact him again. The brunette was kicking himself for not disclosing to Dean that he'd spoken to Crowley in private, but he didn't see what good it would do now. Dean and the gang were on their way up, and that was all that mattered.

Dean leaned down and lazily brushed the back of his hand down the curve of Cas's back, interrupting the accountant's internal monologue. He turned his head and grinned back at Dean.

"You seem in a good mood—happy," the Cas softly observed.

"I could be in a better one," Dean mumbled, tugging at the hem of Cas's shirt until the accountant joined him on the couch. There was the thought in the back of Cas's mind that he should finish his analysis for Chuck, but that idea got smaller and smaller with each fevered kiss Dean placed along his jawline, leading down to his neck until both of them were much too far gone for practical worries.

…

Crowley and Dean's work together didn't go beyond bootlegging and other simple smugglings for the next few months. Dean certainly wasn't complaining about the work and steady stream of money, but he was starting to become perplexed, and slightly worried that they were at a standstill with Crowley—that the British man only planned to use them for "grunt work." Though one wouldn't think it by looking at Dean and interacting with him in public, Cas knew better than anyone (except maybe Sam) that the mobster's self-esteem could use a little work. Dean's image and worth in the eyes of others was a point of contention, and he'd vented as much to Cas in his actions and body language if not so much in actual words. Cas leaned back in his office chair and propped his feet up on the desk, letting his mind wonder to Dean and the gang. Part of him of course wanted what was best for Dean, but the other part of him was scared of anything above what "grunt work" might mean. Cas could make peace with minor criminal activities—he'd taught himself that a _long_ time ago—but he'd never asked himself how far he'd be willing to go. He'd do anything for Dean, that much he was sure of; but how far before his own conscience overwhelmed him? Would Dean and Crowley do something to hurt people? Could Cas condone that, look the other way as long as that light kept shining in Dean's eyes? He shook his head to clear it before he came up with an answer that made him hate himself. He checked his watch. Sally had left about an hour ago and Cas had planned to stay behind and work at least another hour, but he found himself gathering his things regardless. The work would still be there tomorrow morning; Cas needed sleep. He stepped out into the alley behind his office and adjusted his trenchcoat, jumping slightly at a noise. His eyes shot up to find a dark figure outlined by a street lamp.

"Crowley," Cas breathed.

"Castiel. I've been waiting for you. Was about to come knock on the door."

"Pardon my rudeness, but what, uh, what do you need at 9:00pm?" Cas's clipped words betrayed the familiar uneasy feeling slowly creeping back.

"Castiel, me and Dean have been working together for a few months now. I like it. I'd like to expand."

"That's good to hear," Cas replied cautiously.

"M-hm. But you see, I have this problem; contacts—high up contacts and friends—are running into some…money problems. Cops and the IRS are starting to get suspicious. Now, normally I wouldn't give a rip about other people's financial difficulties, but these people's problems directly affect me. So. I ask a favor of you; look over mine and their finances. Come up with something. Get the law out of our hair—just the ones I'm jointed with."

Cas swallowed. "Mr. Crowley, I appreciate your confidence in me, but…I don't think that's a good idea. I work for Dean."

Crowley's eyes took on a different shine, then; the corners of his mouth twitched, and Cas wanted to back away from him.

"But you do more that _work_ for him, don't you?" His eyes locked on Cas's and Cas stiffened.

"I don't know what you're talking about."

"Oh, let's not be silly. You and Dean."

Cas closed his eyes for a second and sighed.

"How did you know?"

"A little songbird told me. But that's not the point. Listen, I'll make this very easy for you. You do this for me, or the next deal with Dean doesn't happen."

"I'll tell Dean," Cas gritted out. "I'll tell him what you just did and he'll be more than happy to break it off with you."

"Oh? And you'd do that? You'd ruin this for him, the only financial stability he's had in a while?"

Cas balled up his fists. Crowley continued.

"This is how the game is played, Castiel. You scratch my back, I scratch Dean's. That's it. I'm not asking you to leave the Winchesters, by no means. Just do a little…private work for me on the side. How about this; I'll give you a week or so to decide."

"I'm sorry," Cas said angrily. "I can't. I won't."

Crowley eyed him for a long time. "We'll see." And with that, he left, disappearing into the shadows of the streets and leaving Cas dumbfounded in the alley.

…

Cas couldn't sleep. It was difficult to work, and worst of all, he'd been avoiding Dean. Every time he berated himself for being stupid, reaching for the phone to call him and just spill everything, something had stopped Cas each time. What was wrong with him? Why couldn't he just do what his heart and logic said was right? But he knew why. He knew why when he closed his eyes and saw Dean, pacing back and forth, shoulders tense, green eyes distant and red from rubbing them. Stress aged Dean, made him look ten years older, and Cas hated it for him. But now Dean had a safety net; he was getting respect, money, partnerships, everything he'd worked at for years. What if Crowley yanked the sheet out from under him? Wouldn't that be cruel, to let Dean have a taste of what he'd dreamed of, only to have it taken away so soon? And here Cas had the power to help. Dean didn't have to know right away, the accountant reasoned; Cas would tell him at some point, when they got further along and really got some traction, and when they no longer had to rely so heavily on Crowley—then surely Dean couldn't be angry with Cas. So when Dean called him a few days later, confiding that something was up, that he was worried that Crowley was backing out, and then how would they ever build back up if Crowley put out a bad word, Cas stopped him.

"Dean," he interrupted. "It'll be fine."

The voice on the other end of the line snorted. "I wish I could be as naively optimistic as you are sometimes, Cas," the other man said fondly. Cas set his jaw.

"Dean, I just have a good feeling. Everything will work out."

"Just like that, huh? You really think?"

"Yes. Trust me," Cas repeated quietly.


End file.
